May is a great time and it would be so nice to be able to do it on your anniversary. How long have you been together? I liked that we would be able to take advantage of the summer/hurricane season rates without the risk of a hurricane.
We live in Union County. I agree with you, prices and expectations around here are crazy. If we had a wedding here we would have to invite nearly 200 people! This would include extended family members who will tell me they haven't seen me "since I was this big", bosses/co-workers, and parents friends. Before you know it....you've spent $40k, you barely ate, and it's all over 5 hours later. Not to say that the traditional wedding isn't gorgeous. I just knew it wasn't right for me and when I told my fiance he, of course, couldn't be more relieved. We just don't have the money to save money for a home and have the big fat Jersey wedding. :-)
The estate is called the Stardust Villa (www.stardustvilla.com). It looks stunning and the owners have been so nice and very easy to communicate with. I'm not sure if you've considered a coordinator (I know some resorts won't allow outside coordinators), but I can't say enough good things about the girl we booked with. We are working with Janelle from Island Bliss weddings (www.islandblissweddings.com) and it feels safer to us to have an "advocate" and point of contact on the island. She is from the states and I believe she moved to St. Thomas after planning her own wedding down there several years ago. I found recommendations from other brides on here for her and my experience so far has been great. She is friendly, professional, and most importantly very quick to respond. We found her fee to be very affordable...plus she works closely with most of the vendors on the island and receives better pricing than you or I would be able to get on our own.
I'm so happy to see another 2012 bride on here...especially from nearby. Doesn't it seem like it's so far away? I hope everything works out for you in your search. How was the pricing for Bolongo? Did you find it affordable for you and your guests?