Thank you all very much for all the advice... I really appreciate it. It's good to hear a range of opinions and a lot of you bring up good points. I especially respect CruisingDad comments about putting USCG in possible harms way when someone does something obviously stupid and gets in trouble.
I will mull it all over... and be getting my boat ready. Regardless of Bermuda, I've got a lot of sailing to do this summer!
If I do head to Bermuda, I'll post on here how it ends up going.