Spaceman,
First of all, we're pilots so there's no shame in asking us anything. Just like yourself, we pride ourselves in knowing everything, even if we don't know shit!
More importantly, I think the answers you've been given already have been awesome and spot on. mcbush, and nsplayr nailed it on the loan vs. invest questions. Rate vs what's the better return, vs what's better peace of mind for you? And I wholeheartedly agree with MtF on the decision to convert. I did this a few years ago for my wife, the second we PCSd and she had her 401K sitting there. We chose to pay a very small tax on it now (even better for you given your situation) and then that thing grows tax free for 30 years. No brainer in my opinion to convert.
I would add a few extra things to think about. I'm no CPA, but I think student loan interest is tax-deductible up to a point ($2500 maybe). I'm too lazy to look it up, but 5 seconds of googling will tell you how much interest you can deduct and what the max income threshold is. With your levels of $$, you'll almost surely be able to deduct it all. $30K at 5-ish% interest is $1500 a year or so in interest, and if you can deduct that full amount, then you're really only paying maybe overall 4% or so instead of the 5%. So that would factor into my "what's the better return" question. Even in today's market and with that deduction, I'd personally still opt for paying off the debt first, then invest (with a small caveat, explained below).
Also, this goes without saying, but pay off the higher interest loan first if you can. Once it's at 0 balance, then pay off the lower one. Even if it's within one account, you can still call and ask if you can apply the payment towards 1 vs the other. I suppose all they can do is say no?
I also agree with MtF about not losing out on your 2016 Roth contributions if you can't pay the student loan off in full first, which you can't at $3K a month. But you have until April 17th of 2017 to make contributions toward 2016 IRAs. Basically you've got until the filing deadline. So I personally would pay off my student loans (higher interest first, if at all possible) aggressively until the point where you need cash flow going to your Roth. With 3 to 3.5K left over each month, I'd pay down student loans until around Jan of next year, then start maxing out the 3-3.5K into my 2016 Roth, to ensure it gets to the fully funded $11K by the April filing deadline, then immediately going back to fully paying down student loans until it's gone, then you'd still have until mid April 2018 to contribute to your 2017 Roth, if for any reason you guys got into a cash flow crunch. My opinion only. And nice work doing this as an O-2. Keep this up and you'll be set sooner than later.