I would suggest calling a local (you can tell by their area code 340) rental company, and get some guidence from them. I about went blind perusing all the villas on the internet, before I called Catered To, told them what I was looking for and was done in about five minutes. Relavant issues to me would be close to town (but not too close) view or water access, likelyhood of nearby construction etc. I have rented vehicles from Conrad Sutton about five times and been very satisfied. I don't have personal evperience (yet) for daysailing but I have heard and read good things about the wayward sailor. Go back and read this board and you will learn a lot!

I can't provide specific comments on your list but Wes has a good idea to get local answers to questions you probably haven't thought of yet.
Before you do call them or begin to limit your selections, make sure you know what you want. Have a good idea of your real budget as that will keep you in check when going down the list. Calypso looks nice right on the water, but the reality is you will be visiting all of the beaches on the island (especially with teenagers). Coral Bay will not have the same selelction of restaurants or services as Cruz and you might not want to make that drive (30-45 minutes) too often. Beautiful, but still a drive.
Terrahawk looks nice and Hawksnest is a great beach but it depends on how short the walk really is.
I personally favor the other selections, all located just south of Cruz Bay and all within 5 minute drive. Great sunsets, close to Cruz Bay services and restaraunts. Klein Bay is next to Rendezvous Bay.
Definitely suggest Wayward Sailor. Captain Phil is great, especially with teenagers.

Chris I intend to "dine" with you at some point when we are there in July. Fact is we will be with kids 16 and 11, with very unsophisticated palates! (Can you do something magical w/ chicken fingers) your assistance on this board demands at least a meeting. I will contact you when we get closer. You are a great ambasador to STJ!