Thread: regular TSP to Roth IRA: any gotcha's doing partial indirect rollovers (conversions)?

Background: over 59 1/2, still working, rolling over partial amounts from a regular TSP to a brokerage account Roth IRA.

From lots of reading this weekend, my understanding is there are two ways to rollover regular TSP money to a Roth IRA:

1. Direct transfer. Print the form on the TSP site, sign and get the brokerage to also sign, get it back to the TSP.
Negative: lots of mailing / faxing, and no taxes are withheld, so then estimated taxes need to be paid (another thing to do!).

2. Indirect rollover: Distribute an amount to myself to my checking account, then deposit into my Roth IRA specifying it as a 60 day rollover.
Positives: simple and can all be done online. 20% taxes are withheld (a good thing as there's no need to pay estimated taxes!).

But, I just want to make sure I'm not missing any gotchas! I'm fairly sure, but not certain, that this type of indirect rollover (regular TSP to Roth IRA) isn't subject to the once per year rule. But, I have yet to find where this is explicitly stated (and I read the entire IRS pub!). I don't want to rollover $2K, then a few months later $10K, buy out of the money call options on 3x short etf's and make a million, and then after some years find out I owe a 6% penalty on that $10k along with my million! (No, not serious, a nice fantasy though ).

So, is it okay to just use the Indirect rollover method w/out worry? It really does seem a lot simpler. I know I'm limited to 4 withdrawals per year, but is there any reason I can't just do such a rollover 4 times if I choose?

I'm hoping some of you have worked out a good practice for doing these partial rollovers. Thanks in advance for any guidance!!