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No, no; I'm not tryin' to proselytize you or hand out Witness phamplets; I saw a Help Wanted KFC sign yesterday which may appeal to those of us who are sick/tired/fed up (I'm in there somewhere) translating taxes for the terminally obtuse. It offers $15-20 an hour (possible manager training for those who can tell the difference between Original and Extra Crispy), 401-K, full health insurance + dental & vision, two weeks paid vacation, and fast-tracking for the skilled employee (if only I'd played basketball instead of majoring in business; accurate burger-flipping is probably a plus). Yes, yes, it's cheap pay, but think of the enticing attraction - soothing that wrung-out, worn-out brain of yours with a desperately needed island-class rest. The only thing you must really know is not PPP ins-and-outs, back-door Roths, or tracking CTC advances, but merely this (50% errors are tolerated): "Did that guy say with cheese or without?"

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You can convert from TIRA to Roth as often as you like. Once done, you cannot undo (or recharacterize) a conversion. If you have ever made tax-deductible contributions to the TIRA, you must pay tax on a portion of the amount converted (in proportion to the amount of tax-deductible contributions). You can recharacterize only regular contributions made during the tax year, NOT conversions or rollovers. The contribution must be moved (recharacterized) by the due date of the tax return (including extensions) for that year. Can you recharacterize a contribution multiple times? I'm not sure - I don't see anything prohibiting it if done before the due date and the trustee is willing to do it. But if you ever called it a conversion, then no. You can also simply withdraw any contribution made during the tax year by the due date (you must also withdraw any income due to the contribution and pay tax on it).

Vanguard is right. Since TCJA it is no longer possible to unwind a conversion. Your client converted a Roth to a traditional, and I don't think that can be recharacterized back to a Roth. Prior to TCJA it could be done. I had a client who kept recharacterizing Roths to traditional and back again during the same year every time the market moved. I had a million spreadsheets trying to keep track of it all and was glad when the law changed just because of him.

If summer or short term work for a foreign employer in a foreign country AND paying foreign tax to that country, your client will have a foreign tax credit on his federal return. If it's a high tax rate country, that can be a valuable credit.

It might not make a difference between a non-deductible Traditional IRA and a Roth, if Congress passes the laws they're discussing! But you have to track (Form 8606) his non-deductible Traditional IRA contributions anyway. I'm all for him doing the conversion to a Roth now. However, if he has a lot in his TIRAs so that his non-taxable conversion amount would be small compared to the taxable amount per the ratio determined by all his TIRAs, it might not make sense to convert. He would make that decision. Not his broker! Tell him to ask for a supervisor. Or, if a large national brokerage, their tax department. Or, move his retirement accounts elsewhere, and then do the backdoor. (I'd do that last one, if it were my money.) Sorry, I didn't understand the timeline in your OP, so I wasn't addressing your issue.

Completely unrelated but interesting case: https://www.propublica.org/article/lord-of-the-roths-how-tech-mogul-peter-thiel-turned-a-retirement-account-for-the-middle-class-into-a-5-billion-dollar-tax-free-piggy-bank Summary: Guy who founds Paypal (before it went public) is given stock with an ultra low cost basis as part of his salary contract. The cost basis is deemed $1,700 so he puts the shares into his Roth IRA. The company goes public shortly after that and those shares are worth well over $100m. He does this multiple times with different companies and his Roth IRA is now worth $5 Billion which he'll never pay $1 in tax on if he holds off on withdrawing. Yes it's all strictly prohibited but the IRS never audited him. You would think a $1,700 Roth value going up 9 figures in one year might draw an audit flag. First, he was a principal in the company so that's a violation. Second, he contributed stock and not cash which is prohibited. Third he valued the shares at far below market value and the IPO disclosures of the firm outline they were below market value.