Its actually not that bad at all, it took me ten minutes, tops. Call the FCC number/online help number, I forget which, they answer the phones super quick and are very pleasant. Say you're applying to an airline and you need your RRTOP and they'll either walk you through it or tell you the numbers of the forms. There's one form to fill out with your info on it, but pages of explanation, so its a bit intimidating, but not biggie, and there's another form so they can process your fee if you pay online. Done. Three days later, mine was in the mailbox. (With a frameable version! Joy!) $55.
Edit: I've heard through the grapevine that if you screw up and send them the money and you missed a hoop, you've lost the $$$ and you have to repay for the next one. This I heard from a co-worker who heard it from a friend, so I'm not saying its accurate, but bewarned! That's why I called and chatted up the nice lady.