I guess I'm part of the club also. I started taking classes at the Cocounut Grove Sailing Club in Miami, in 2009. I tried renting one of the club boats on weekends and could hardly get one (812 members and only 178 members with boats). So I began looking for something similar to the 23' Ensign that I learned on.
I found a local non-profit organization that received boats as a donation and they would then sell them. I ended up picking up a 1976 23' Carl Alberg Sea Sprite a few months later. She had a 5HP Nissan kicker, a good main & jib, roller furling (cage had to be repaired) and two Lewmar self tailing winches.
I ended up taking her out of the water, scraping barnacles off till my fingers bled, sanding the bottom, fixing a few dings and dent, painting the bottom with anti fouling paint - which I found out has to be done every few years. Spent a lot of time on the electric, getting light inside and outside working. Finally got her in the water after three months of working on her.
I've had her now for almost two years and I'm in the process of moving up in size to a 33' Pearson with a drop keel. Yep, I want to live aboard also. I figure $600 a month for a slip is cheaper than $1800 for a one bedroom apartment in Miami and a lot more fun.
My friends think that I'm crazy, but I ask them if they can take their apartment with them to the Keys.
Enjoy your Journey!