Just re-read the whole thread for nostalgia sake and realized I never posted updates from our trips. Went in December and April and had an amazing time both trips. Stayed at Carl Gustaf in December for 8 days, which I would highly recommend for first-timers. It's right in town and we really felt it helped us get a lay of the land not knowing anything. Stayed in a villa in Colombier for 2 weeks second trip, which was great. I think I'm team villa from here on, but there are pros and cons to both for sure.
I've spent way too much time researching villas and hotels (and pretty much everything St Barth related). Plus I feel like we've crammed a lot into our short time there as pretty much every day consisted of some kind of beach club with lunch out during the day and some kind of restaurant at night, so hopefully I can provide some decent info. We never did the picnic on the beach thing, although we always talk about it and I really want to try that sometime. We also cooked very few meals at the villa. Way too many to list, but here are some of our favorites...
Restaurant - L'Isola
Hotel - Eden Rock (Cheval Blanc close second)
Beach Club - Gyp Sea
Day Party - Nikki Beach on a Sunday (but that's kind of an outlier as there's really nothing else like it on island)
Night Party - La Guerite on a Wednesday (but we've had great times at a lot of them - also, there are definitely certain nights that are better than others at certain places)
Rented a car the first trip and never drove it. It literally sat the entire time without us ever getting it out of the hotel's valet. So, we didn't get one next trip. Had a driver take us everywhere, which we prefer, but I can see how some would prefer having a car. As others have stated, if you get a car, Mini Cooper seems to be the way to go.
We go through San Juan and fly in on Tradewind and they are amazing. I doubt we'll ever do it any other way. It's a bitch to get to St Barth, but worth it in my opinion.
Honestly, I don't have a negative review of anywhere we've been at all. Sometimes you get some snobby "French asshole" attitude on service, but it's pretty rare and you just have to kind of learn to deal with that being part of the culture. It can happen anywhere (except L'Isola because they're all Italian) but for the most part, everyone is lovely.
We have definitely fallen in love with St Barth. We've made lifelong friends with people who live there and all over the world. And, although I was busting his balls in my last post, @wild_turkey showed us noobs a great time our first trip, so big props to him and his wife for showing us the way. And thanks to everyone else on this thread who got us to go. Can't wait to go back.