Welcome to FT!
You might have already answered your own questions, but it is still good to get other's opinions. As a UA flyer I would suggest you fly on United. You can sit in Economy Plus (free for elites, or you can pay for an upgrade at the airport), and channel 9 allows you to listen to ATC!
If you are a true FTer you would not fly direct -- the more the connections, the better. Well, that's how I think anyway. See this thread for a discussion on what program to use out of Boston:
http://www.flyertalk.com/forum/showt...ghlight=Boston.