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I rolled a 401K held at Vanguard to an IRA at Vanguard in 1997. Very easy to setup if you can stay with the same fund family. They did most of the work. Even if I had wanted to move the funds to another fund family I think I would have done the rollover with Vanguard first to avoid problems. The IRA could be transferred later.

Not positive but I don't believe you can rollover from a 401K to a Roth IRA. Also, if you've made after-tax contributions to the 401K, they will be returned to you. You've already paid the tax so just invest them in a taxable account.
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