AJ
Level 6

Get your taxes done using TurboTax

I could have used a better choice for words there. The process is probably "straight forward" even with multiple withdrawals.   Just be sure to keep your Forms 8606 and your Forms 5498 and know your basis.  I've encountered some people who do OK making their first withdrawal and then they lose track of their paperwork and make mistakes about their basis in following years.  If you are organized, then there should not be a problem.