Thank you to everyone for your help and suggestions on this. I took my PNR to the AA office downtown and it was ticketed--of course there were a few hiccups during ticketing but I'm not surprised given the complexity of these things. The nice lady ticketing my itinerary had never seen a RTW before, and I was the talk of her office for the rest of the day.

Here's what I learned from all of this: aside from having to queue your ticket for pricing, RTWs can be just as easily DIY'ed as, say, BDA-BOS-BDA for the weekend. If I didn't want Bermuda ticketing (see above for why I did this) I could've easily ticketed this myself.