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Greetings, SRW, and welcome. You asked:

<<1) Is there a good/bad/doesn't matter time to roll over monies from a previous employer's 401k/403b into a Rollover IRA (I'm thinking of market fluctuations, etc.)?>>

In other words, you wish to time the market. Most Fools recognize that the pros can't do that with any long-term success, and neither can we. Therefore, assuming you intend to keep the same type of investments in your IRA as you have in the 401k/403b, the "when" of a rollover or transfer has little or no impact on the long-term results.

<<2) Do you have to first roll over into a Rollover IRA before converting into a Roth IRA? What are the restrictions regarding this?>>

Yes, you must first get the plan money transferred to a traditional IRA. Once there, it may be further moved to a Roth IRA. You will avoid any and all problems by ensuring the transfer of money from the plan to the traditional IRA and from the traditional IRA to the Roth IRA occurs directly between the custodians involved. In other words, you do not want to receive a check you can cash at any point during these transfers. To arrange for direct transfers, just ask the custodians involved what you need to do. They will guide you through the administrative steps you need to take.

<<3) About the first time home buyers $10,000 withdrawal without penalty exception, should I convert my existing Traditional IRA into a Roth IRA before I take the $10,000 withdrawal to avoid paying taxes on the withdrawal?>>

Yes, but taxes will only apply to any earnings you take from the Roth because you will already have paid taxes on the money you transferred from the traditional IRA. If any earnings are part of the $10K you take, then to get them tax-free the transferred money must have been in the account for five tax-years. Otherwise, you will pay taxes on the earnings taken. And you might not have to touch earnings at all because the first money out of a Roth is considered money from contributions. It all depends on how much you convert from the traditional IRA.

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