401k Rollover

Generally I just open a traditional and a Roth and then it's easier to do a conversion after all the funds are out of the 401ks. You have an option to withhold taxes on the conversion.

you are taxed on a roth conversion. you can either send the money directly from your account to the govt. or you are going to get a 1099 at the end of the year to pay it. the only thing you are avoiding is the 10% penalty

no you can. actually most institutions will automatically withhold 10% unless you specify that you don't want any withholding

Whatever dude, do what you want but w/h that $ from an IRA for the purpose of a conversion will result in a penalty.

I.e. I convert a $100k T IRA into a Roth and w/h 20% ($20k will be considered a distribution and penalized an taxed).

And that 20k has now exited your IRA and considered a distribution... lol

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no you can.

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Whatever dude,

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ok I stand corrected thank you

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Also, was looking at going Vanguard, however my current employer uses Vanguard for 401k. Is this something I should avoid from a diversification perspective and if so, any reccs on a mutual fund company to look into?

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There is no diversification issue in going with Vanguard just because your current employer also uses Vanguard. Diversification would have to do with how your investable funds are allocated. For example, having 100% of your investable funds allocated to S&P 500 index funds (Healthcare ETFs or whatever) at Vanguard and Fidelity or Vanguard and T.D. Ameritade would not make you more diversified. Although I don't have an account at Vanguard, I do hold some Vanguard products in other accounts. They tend to be some of the lowest cost investment funds out there.

As for the first part of your question in the OP, the best thing to do would be to call customer service at Vanguard (or whatever company you choose) or a tax professional, and ask that question.