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He's had his Roth at UBS, where we have our accounts for the time being, since inception. The TIRA was created to take the company contributions from his Roth 401K. The TIRA is being converted to the Roth and there will only be a Roth IRA to transfer.

Okay. If he was intending to transfer the UBS Roth account to Vanguard anyway, I still would have suggested he just move the 401(k) money to Vanguard in the first place. He still would have had to deal with transferring the UBS Roth IRA to Vanguard, and probably would have still would end up paying a $95 fee.

Since he will be getting out of the positions he is in anyway, how much of a tap dance would it be to just take possession of the funds directly and roll it over ourselves?

Those are considered rollovers, and he will have to abide by the 1 per year limit, and the limit of 60 calendar days to get the money into another IRA. Additionally, he will have to ensure that NO taxes are withheld from the account, since he's presumably under 59 1/2, and those withholdings would be subject to taxes and an early withdrawal penalty. Since many brokerages (not sure about UBS) have a default withholding rate that's not zero, you often have to do something extra to ensure that taxes aren't withheld. And if somehow, they end up withholding them at the default rate anyway, it can really mess things up.

Since he will be getting out of the positions he is in anyway, how much of a tap dance would it be to just take possession of the funds directly and roll it over ourselves? I have multiple accounts I need to do this for, having my own Roth, Traditional and Inherited IRA. Only 1/year allowed per person? Since the inherited IRA is under Dad's name, would it count against me?

It's 1 per year for each type of IRA a person has. So the Roth and Traditional would each have their own rollover allowed. Since the Inherited IRA was inherited from your father, so that you are not able to treat it as your own, it's titled differently, and so it would have it's own single rollover per year.

That said, if you are moving these all to another brokerage, why wouldn't you ask that brokerage to initiate Trustee to Trustee rollovers for each account? I have found that the receiving brokerage usually has a lot more interest in getting the accounts moved than the disbursing brokerage, and will figure out a way to make it happen, while the disbursing brokerage can put up roadblocks so it's harder to make the transfer happen. And I would prefer to not lock myself into being prevented from doing a rollover where I take possession of the cash for a full year, just in case I find myself in a situation where I would want to do that.

Have you (or anyone else) ever had luck with Vanguard doing this?

I haven't ever asked Vanguard to reimburse fees, so I don't know if they will. But it can't hurt to ask. If they say no, you can always look around for another brokerage that will reimburse fees, or is at least offering an incentive that will pay back some/all of the fee. You may want to wait until early 2019, since the IRA transfer offers seem to be sweeter between Jan 1 and Apr 15. Even Merrill Edge often ups their amount offered from $600 to $900 during that timeframe.

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