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On that note, is it a losing proposition for me to liquidate and then repurchase shares (within the 60 day window)?

This should be fine, and is basically what I've done each time on my 401k rollovers, about four times now in my life. You want to make sure to liquidate inside the 401k, have the cash transfer over to Vanguard, then buy again inside Vanguard. Done correctly, this isn't a taxable event, since the sell and buy each happen inside tax-sheltered accounts. You do risk missing a jump in market prices during the interval, but of course you could also miss an equally sized market drop, so that washes out.

- Erik
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