After looking into this further our options are somewhat limited due to flights. I have to fly out of Orlando after dropping off the kids. So after looking at flights I think we can only reasonably go to
St Thomas (or surrounding islands)
Puerto Rico
Costa Rica (already been to Arenal and Manuel Antonio)

We've loved St John and are leaning towards going there again (although I am still intrigued by exploring another area of Costa Rica). My question is,,,, what is Virgin Gorda and Tortola like in comparison? Do they have a center like Cruz Bay? Whats the vibe? Wondering if its worth checking it out or if we should just stick with what we know.

Virgin Gorda is similar to St. John but has a much smaller "town". Tortola is much more populated.

I'm intrigued by your question since you say "flying" logistics make it hard for you to get to St. John yet you are considering Virgin Gorda or Tortola. If getting to St. John is too difficult for you then you'll probably find it just as difficult to get to Tortola and even more difficult to get to Virgin Gorda.

Soryy, don't know any "1 bedroom" cottages" on St. John but suggest you look at Gallows Point Resort; Estate Lindholm or Gecko House - they may be just the type of places you are seeking.

My impression was that you can get a ferry from St thomas to either St John or Tortola or Virgin Gorda. If I am wrong, please let me know! The flight is complicated because I am flying out of Orlando (where I will be dropping the kids with grandparents) and my husband is flying out of NY. I want to find a flight with a stop in Orlando so I can jump on board with him to avoid getting to our destination at different times. JetBlue has a major hub in Orlando, and has flight direct from Orlando to Puerto Rico, St Thomas and Costa Rica.

In my research Ive come across Vieques too -- which looks very interesting. If anyone has input on how it compares to St John I would appreciate. Im worried it doesnt have much of a town.

Yes, you can get ferries from STT to St. John, Tortola and Virgin Gorda. But like I said, if you find it difficult to get to St. john you'll find it more difficult to get to Tortola and Virgin Gorda (not impossible but more difficult).

No I don't find it difficult to get to St John. My point was just that my flight arrangements are difficult to arrange and it limits where we can go (ie, we can't do Aruba, Turks & Caicos, etc because there are no stopovers in Orlando).
Our options are therefore limited to St John, BVI, (both via St Thomas), Puerto Rico, or Costa Rica. Not a bad problem to have
Thanks for your help.