McGookin had a nice summary. I'm certainly no expert, but I lived there briefly years ago. Islamorada gets my vote, Upper Matecumbe Key is one of my favorite places there, but housing is going to cost you and arm and a leg, not much land there. As far as schooling, it seemed like a lot of the locals sent their kids to Island Christian School, but Coral Shores High in Tavernier was the main school and probably the best in the Keys. I though Key Largo was tacky, but it's closer to Miami. I never did explore the "big" lower Keys, like Big Piney Key, but they would be the most peaceful place to be. Key West, touristy. One thing to consider is getting out for a Hurricane. I went to church with an old guy that survived the Labor Day storm in 1935. Things can get rough there. Islamorada is a lot closer to the mainland, and you still have to get through a 29 mile stretch with basically nowhere to get off the road. If anyone reading this happens to visit the Lorelei, toast a drink to me.