SW Florida Boat Choices/Advice
Hmm....36foot and under 5ft draft would most likely put you into a wing keel or swing keel. (obviously there are pro''s and cons to both--Check the archives). There are a lot of boats that fit your criteria. But since you were fairly happy with your C30 then another boat I would say to look at is an older Catalina 36 wing keel (4''6" draft). You should be able to find an older one (around 1983-1987) that would go for less than your budgeted amount. It has a very good history (still in production and over 2100 built) and most people that have one praise its sailing characteristics. It is really a great coastal cruiser, but I know of more than a few people that have taken it blue water sailing and have been happy with it.
Take a look at the Sailnet Mail list. There is one for the C36 and you can ask there or go through the archives. Also go to http://www.catalina36.org/ they have a strong association and lots of info and helpful people. Good luck.