BWWB...based upon your latest comments I am still gonna suggest you look at Cape Dory...but a 33. Fits your budget...easily rigged for singlehanding...full keel heavy displacement boat and pretty! All within your budget.
Rick..your budget of $1200/month is realistic I think if you are on the hook but on a dock with air conditioning (YES YOU WILL NEED IT IN FL!!) is probably a bit light for Florida. I would suggest a minimum of $1500 a month if you can find decent dockage in not too ritzy a place that accepts liveaboards. (Finding live aboard dockage my be your biggest problem.)
What Dawg is suggesting with his 15-20% is that on a $100k boat you should also figure on spending $15-20k on upgrades, repairs and adjustments once you get the boat. This is an average and is HIGHLY dependent on the state of the boat you buy. On Camaraderie...we spent nearly 50% of our initial purchase price...but we knew that going in. The key is to know what you are getting into up front! Once you've made that initial investment and upgrades, you might want to budget around 10% of boat value annually for repairs and maintenance. Some years you will spend way less and others way more....but sooner or later stuff happens!