SW Florida Boat Choices/Advice
When searching for a boat with a shallow draft but cruising accomodations at a certain price point, you will find your choices quite limited. But there are some gems.
Jeff H has a great list, which is based on a lot of experience. I used to sail deep keel racers off New England but am now a convert to the K/CB design. As Duane mentioned, I have a Hood 38 that has provided me the best of all worlds.
A couple thoughts I had in reading this string. The Pearson 365 has a PHRF of 210. I think there is a great benefit to a boat that can provide you with speed, power and pointing ability. The P365 does not seem to do that. I think it is not only important in day sailing but in cruising, as you will meet a greater variety of conditions.
And there is the issue of cruising accomodations. This is something that needs to be explored on a personal basis. But generally, LWL, beam and displacement will be some indicator of the space down below.
Pearson did make a CB ver of the 36...a nice boat with a lot of accomodations for a 36 (I believe a large aft berth). It may be out of your range.
Given all your considerations, I think you might look more closely at the Tartan 37. Nice build quality and very good sailing qualities. They were built over a somewhat lengthy period of time and I believe that some may be coming down to your price range.
Other than that, I think the accomodations of the Catalina 34 and 36 cannot be beat in this price range. It is simply a question of the downside of their wing keels and their suitability for your desired cruising grounds.
Hope this helps.