Catalina 27s are great boats and are available in good shape for $10,000 and under. I would think that compared to a teardrop trailer it will be the Ritz. Another boat that I. think offers good value is the Cal 28.
Basing out of the Fort Meyers area would provide lots of cruising areas within reach and reasonable hard storage within reach. The east coast of Florida offers better wind, better access to the Bahamas and NC but does not have as many cool places to go IMO. Maybe start in SWFL and as your abilities and confidence grow move to the east coast. Have fun, David