Hi JP, I think you have gotten a very good review of Longboat from the answers provided here by my fellow realtors. I will add however, that yes, in my opinion there are dramatic differences between all of the barrier islands between Anna Maria, Lido, St Armands, Siesta and Casey Key. All have their pluses and minuses but all are subjective to personal appeal. Mainland properties in Sarasota and Sarasota County, also have wide varying differences and can only be appreciated by a visit and learning first hand what makes each one tick. There are also many different architectural designs from Florida School of Architecture, Florida Cracker, Bungalow, Spanish, Contemporary and Mediterranean Revival.
I hope this has been an added benefit to your question.
All my best,
Teresa M. Fellows
Waterside Realty LLC