More re @derf’s query about % of transactions that go bad. Bear in mind that not all “transactions” are equal. I can’t remember an exchange between funds @ TRP ever failing to go through. Pretty routine stuff. Here’s where it became frustrating for me ……
1) Switching from paper statements to online statements as my internet capability improved did not result in fewer paper statements as intended. The opposite happened and they began mailing monthly statements that I did not welcome - often replete with account numbers and balances. So I called them. First they said I had to remove checkwriting capability from my money market account if I wanted these frequent mailings halted. I did so at some inconvenience to me. But the flood of paper did not stop. If anything it increased. Calls to try to resolve this often had me on hold for anywhere from 30 minutes to 2 hours. Still, the monthly (occasionally weekly) paper statements continued to arrive. And every “agent” I talked to seemed to have a different “take” on what the problem was.
(2) For years TRP had agreed to stop taking Michigan withholding from distributions provided I filed the appropriate Michigan tax form ahead of time. And every January 1 I completed a new form and sent it (certified mail) along with a brief typed letter to Price. But when I took a 2021 distribution mid-year, they did not honor that opt-out form. To be more specific, they did honor the opt-out provision on part of the distribution (from one bond fund) but they pulled the state tax from the other part (from a second bond fund). When I followed up with a call to try to ask why they essentially “blew me off” saying something like “sometimes we do and sometimes we don’t” (honor the opt-out request). Interestingly, Fido let’s you opt out of state withholding when you submit the transaction - a feature missing at TRP.
(3) While 90+% of the transfer to Fido was in-kind, there were 3 short term bond funds having small balances I elected to liquidate. Rather than combine these into a single check, Price mailed Fido 3 separate checks. Fido credited those to my account and allowed me to trade with them, which I did. But 3 days later Fido had the checks returned to them from their bank as “unpaid.” The next thing I knew my investments were being force sold by Fido and I was being hit with a slew of related fees. I was suspended from being able to trade with unsettled funds for 3 months. My record still bears a “Free Riding” violation which the SEC considers fraudulent behavior and a serious breech of law.
(4) Daily for over a week I was in phone contact with TRP, experiencing those 30 minute to 2 hour wait times on virtually every call trying to resolve this. Their phone personnel seemed poorly informed and ill prepared to deal with the issue. Repeatedly I was told “we’ll call you” which rarely really happened. They did eventually apologize for the matter and send out 3 new checks to Fido. What a horrendous experience - considering that TRP had long held the bulk of my retirement assets and had been trusted by me for decades to do things right.
So, @Derf and others …. it’s not so much the % of things that go wrong as the type of issue involved and how well equipped they are to resolve a problem once one occurs.

@Sven. i guess you meant "outside" of the US. The fellow I finally reached was surely a first-language USA English-speaker. But clearly, TRP is not keeping their end up. Just awful. Years ago, I was sent a card in the mail with a "Priority" phone number. I guess you have to be some kind of special to receive the thing. But there's no "priority" service about anything to do with TRP, anymore.

WeathTrack and Morningstar In-depth interviews are far better than CNBC. What can you talk about in 5 minutes slot, really not much.
Giruox gave a detailed interview last spring during the lockdown (he was doing it from home). Will post that agin when I locate it. He talked about the change of management that led them to buy GE at very good price. Their team know the companies well and forecast their earning several years ahead. The stable stocks revolve around healthcare, consumer staples and utility stocks. Took a more tactical approach on Amazon and Microsoft. That fits his approach being GARP and don’t overpay for growth. He explained his view of bank loans and how offer attractive yield (3%) with less than one year in duration. Think I will get his Kindle book over Christmas.

1 - 1 - 1
The last profitable day for initiating a buy-and-hold position in ARK Innovation was one year, one month and one day ago. Somewhere in the mid-day. Good news, I guess, is that any purchase made after that day is a candidate for tax-loss harvesting.
64.9%
The amount by which ARK will have to rise for get positions established in early February 2021 out of the red. The fund saw huge inflows in the fourth quarter of 2020 and most of the first quarter of 2021 as investors rushed to buy the previous five years' returns. Which is to say, almost all of ARKK's investors are likely underwater.
- - - - -
There's an interesting (somewhat semi-pro) piece on Wood's long term record at the anonymous InvestmentWatch blog. The author's takeaway is

almost all of Cathie’s major outperforming years come during special periods in the market cycle, particularly in the periods following a market crash ... Outside of those special events, Cathie’s funds generally underperform equivalent style peers on a year-by-year basis. She has a history of leaving a fund during or following a period of underperformance, then “rebooting” in another fund. This includes a short stint in a hedge fund that lost over 80% of it’s AUM.

That last caveat shouldn't apply now, but the others are useful reminders.
For what that's worth, David

FWIW...I just completed an DB plan rollover to my exiting TRP IRA Rollover (Brokerage). It was seemless and I had no need to interact with TRP.
A few years ago, when changing jobs, I tried rolling my 401k at former employer into Fido (new 401k at new employer) and had issues with a small amount of the proceeds considered 'after tax' money from the sale of company stock. Fido wouldn't process rollover so I switched to tRP. They obliged and asked for a Letter stating what to do with after tax $$$...simple fix!!! TRP received my proceeds because Fido couldn't accomodate me...

I've had an account with TRP for 20 years. The brokerage customer service is solid, the fund lineup is a above average IMO. There 'Sales Charge' is $35 compared to Fido's $49.95 so that's better. I like Fidelity's fund screener much better...it's probably the one area TRP is below average. Hope that helps or if you have any particular questions...

Wow, what a mess!
This is even worse than the Facebook mess (and no customer support) that my wife has encountered (locked her out of her account), because money and tax law are involved in your case.
Several years ago I opened 529 accounts for my two grandsons at TRP (the state of Alaska plan). I mailed in a check to fund the accounts.
Check didn't clear.
Waited a little while. Called TRP.
Waited a little longer.
Finally they said we've not received the check -- I should send another.
So I agreed to send another check, with the admonition "don't cash the first check!"
Second check arrived there and was deposited in the accounts.
Several weeks later, they returned the first check to me. I'll never know whether they had it all along or it was lost in the mail. I should've stopped payment on it.
Fortunately it all worked out.
The boys are now high school juniors and looking at colleges.
Which TRP fund did you choose to put the transferred funds in? How were you eligible to put money in the closed fund?
David

The biotech space is very volatile though one which I have involvement. As noted above, IBB and FBIOX are good choices which contain several well known and familiar names and with good overall portfolios. There are funds with a more clinical stage focus, such as ETNHX. I've owned that for about 6 years with good results, though it's not for the squeamish. As Mark noted, FSMEX is an excellent choice in the healthcare space. I swapped VGHCX for FSMEX last year, and frankly, should have done it years ago. That one's a Great Owl, and deservedly so.

I've also had good experiences with Tire Rack over the years.
My last tire purchase (several years ago) was at Costco.
Costco has a much smaller selection of tires since they only sell a few different brands.
However, it's possible to get a great deal if the tires you want are available and one of their periodic sales is in progress.
Their service is top-notch although I've waited longer than I've liked for work completion on several occasions. The tire department at my "home" Costco always seems to be busy!

@BenWP - Size 265/65R-18 - Japanese off-brand. They ship UPS in 3 days. Yes, I have a local dealer who’s happy to mount & balance them, for a fee of course. These are a mud & snow tire suitable for both winter and summer driving. Have had good luck with Tire Rack over the years.

FBIOX, Fidelity's Select Biotechnology was a standout performer in the recent past but I have no idea where they stand today. Just wondering if you've also considered ETF's as a possibility. You might also look at some wide-mandated health care funds (e.g. PRHSX) to see if they may contain healthy slices of biotech holdings.
The health care sector has been hit or lots of misses for me over the years and I've settled on just one that I care to hold longer term - FSMEX.

Originally I'd hoped to name this site FundWatch.com. A squatter in the Netherlands wanted $25,000 for the URL so, no. (Mercer now owns it.) To the extent we have an active going-forward, it would be good to find a way to signal the fact that we care about pooled investment vehicles (PIVWatch?) and recognize that the wrapper makes a difference in only a few special instances (you can't close an ETF to new investments so in a capacity-constrained strategy, you need an OEF, as an example).
Cheers and holiday good wishes!
David

Interesting observations.
I looked up fundwatch.com and there is mercerfundwatch.com, a fund advisory for HK and Singapore. This "Mercer" (not related to the "Mercer family" in news in recent years) is a subsidiary of Marsh & McLennan/MMC.
I think that MFO - Mutual Fund Observer name caught on nicely.
There have been several instances where creation/redemption processes for ETFs were disrupted and then they traded just like CEFs at premium/discount. Of course, ETFs are not designed with this in mind, but that can happen. And ETNs (terrible sponsor IOUs) are famous for shutting at the worst possible times for their holders.

Thank you everyone for your contribution to this topic.
@msf, great stuff to consider as I am working on the $ amount we want to convert. Most likely it will be done over several years before RMD begins while coordinating with my spouse’s RMD which starts several years later.
@hank, we did exactly what you suggested several years ago when we consolidated IRAs in the same brokerage. We have laid our a plan on what goes in the Roth versus Traditional IRA.
@sma3, I have been reviewing the details on income level and their impact on Medicare premium. Great suggestion on Maxifi for evaluate various scenarios - will check it out.

I feel that longevity insurance is one of the few useful products that the financial industry has created in the past several years. That said, if it's not a product that you are interested in independent of tax considerations, then buying a QLAC is a poor way to reduce RMDs.
Kitces, Why A QLAC In An IRA Is A Terrible Way To Defer The Required Minimum Distribution (RMD) Obligation
https://www.kitces.com/blog/why-a-qlac-in-an-ira-is-a-terrible-way-to-defer-the-required-minimum-distribution-rmd-obligation/
Getting back to timing of conversions ... Though recharacterizations (undo's) of conversions are no longer allowed, there are a couple of other tactics that provide some or much of the same effect.
One is to use a recharacterization that is still permitted. A contribution as opposed to a conversion can still be recharacterized. So if you contributed $6000 to a Roth IRA in 2021 but in doing your taxes you discover that you'd have been better off taking the deduction, you can recharacterize the $6K as a contribution to a traditional IRA. (You can also do the opposite: contribute to a T-IRA and then recharacterize it to a Roth.)
https://www.irs.gov/retirement-plans/retirement-plans-faqs-regarding-iras#Recharacterization of IRA Contributions
Another it to take advantage of the 60 day rollover rule (sometimes limited to one per year). One could withdraw money from a T-IRA near the end of the year, and then early the next year when the tax situation is clearer (and within 60 days of the withdrawal) either put the money back into the T-IRA (60 day rollover), put the money into a Roth (indirect rollover conversion), or split the money between a T-IRA and a Roth.
If any money goes back into a T-IRA, you can't do this again for another 365 calendar days. The restriction is according to days, not fiscal years.

I can't read Mark's article, need a subscription.
@sma3, what do you mean by this comment:

It is pretty sad when your bonds and bond funds loose money all year but the alternative for bear market protection- cash- is worse.

Why is cash, that may have little to no appreciation, worst than bond funds that, well, many think will lose money going forward? One, cash, has loss of value per inflation and the other (bond funds) has loss of capital value + loss of value per inflation. Or am I missing something?
Also I would say, yes, TIPS have lost money most of the time over past years, but inflation during those years has been nil. Of course they would not perform as well as a core bond or most any bond fund in that environment. But the inflation rate is changing, quickly. The time may be coming where they will out-perform core bond funds for years to come - ok, maybe.

@ Hank
Does it matters what you convert, if you can always buy or sell anything in either account tax free?
Once you have the capital in a Roth, I agree it should be probably devoted to more risky, long term investments.
Converting before you are on Medicare and after are two different calculations.
It is important to remember that the IRMAA surcharges go from zero dollars ( B Medicare Premium $1776 /year in 2021) to $700 for ONE DOLLAR of income ( AGI before the standard deduction) above $176,000 for a couple and $111,000 single. A couple would therefore pay $1400 extra.
IRMAA is based on two years before 1040, so 2022 will look at 2020 AGI. Once you file 2021 taxes in 2022 you can ask for redo, if your 2021 income is lower. It takes a month or so, so you will end up paying more for a few months.
One strategy I am considering is to do a large conversion, all in one year, before I take SS at 70. Then the impact of the conversion on the IRMAA will be limited to one year.
Other things to consider. IRS lets you put up to $135,000 in a QLAC which will reduce you RMD proportionally.
Lawrence Kotlikoff from BU has a great article in Barrons
https://www.barrons.com/articles/most-retirement-planning-is-wrong-laurence-kotlikoff-51631207476
He also runs a web site with a neat financial planning program for $100, Maxifi. It may be overkill for a lot of folks, but it will allow you to run all sorts of projections and scenarios about Roth conversions pretty easily

@David - I am truly sorry to hear of your loss having lived through the same just a few short years ago. It's heartbreaking and I can only echo your sentiments regarding expressions of love and caring whenever you can, and as often as you can while you can. Peace.

Thanks for the note from my Barron's summary this AM. People know where to find it.
"COMMODITIES. The auto market (new or used cars) is very tight. But PALLADIUM (-26% YTD) and PLATINUM (-14% YTD) are down sharply because of the drop in auto production caused by SEMI CHIPS shortages. This is unusual as most commodities are strong (S&P GSCI commodity index +28% YTD). Palladium is used more widely in the catalytic converters of gasoline-powered cars while platinum is used more in diesel-powered cars; although either metal can be used, there are large capex costs for the switch for the manufacturers. Rebound in palladium may be dramatic when the auto production picks up as chips supply-chain issues ease. On the other hand, platinum demand has fallen sharply for investments and also for other industrial application, so there is now a platinum surplus. Platinum is also much cheaper than gold (it used to be the reverse years ago)."

The question can be split into two parts:
1. Best time during a given year
2. Best year
1. In theory, the best time within a year to convert is when your T-IRA portfolio is at its nadir. Which is great if you can see into the future.
Pragmatically, waiting until there's a market correction (10% dip or more) can leave you converting at a higher value than converting now. If the market rises 15% while you're waiting and then drops 10% (to 103.5% of your starting value), what's the point? Or if you're planning on converting a bit each year, you can easily wind up stuck at the end of the year with a higher market still waiting for that correction.
If you're trying to keep MAGI under a certain "cliff" threshold (e.g. for ACA subsidies or to avoid IRMAA) then you should likely be conservative and top off your conversion near year end once you have a better handle on MAGI YTD. If your concern is about edging into another tax bracket, it's not a big deal if you wind up a few dollars over or under, so don't wait until year end for that reason.
2. If you're converting and paying taxes with non-IRA money, sooner can be better than later even if your expected tax rates in the future will be a little higher. That's because you're effectively adding money to your IRA by prepaying your taxes. (A dollar in a Roth is worth more than a dollar in a T-IRA.)
OTOH, many states give tax breaks for retirement income (including Roth conversions) once one reaches a certain age. So it can be advantageous to wait until then. You might convert between the time you reach that age and the time you retire and actually start drawing money from your T-IRA and/or pension (and possibly using up that tax break).
Several states give some sort of help on Medicare Part D prescriptions, where your income needs to be low enough to qualify. Doing Roth conversions earlier (even at somewhat higher tax rates) may help qualify for these or other income-related programs.
The largest such program is EPIC in NYS. Its income cutoff is decidedly middle class: $75K single, $100K married.
The rule of thumb short answer is the sooner the better (both within year and across years); just don't do too much in a single year and keep various income thresholds in mind. And if you're thinking of making charitable contributions, keep some money in the T-IRA so you have it available for QCDs.

Gentlemen, I really appreciate for your inputs. Last spring was a great opportunity to do a large conversion. Unfortunately many of us did not plan for it. Now we are evaluating which how much and which funds to convert per year. Great reminder that the tax table is for the adjusted gross income.
To reduce tax in retirement, we did few small changes. We switched our 401(K) to Roth 401(K) several years ago. Still we have rollover and traditional IRAs to consider for higher future tax and RMD. Higher retirement income incurs additional cost on Medicare premium and taxation on most of the social security benefit.