Originally Posted by zedboy
There are a lot of good boats out there, and it's a buyer's market. But you have to figure out what you want - full keel/fin keel, aft/center cockpit, traditional or modern, lots of teak or none.
Go walk the docks with a cold six pack. Sailors love to talk about their boats - go see what's out there, and try to get a ride on as many as possible.
Also read up the boat inspection threads here and elsewhere. Hire a good surveyor, but the more you know to ask the more a surveyor can teach you.
Good advice above about trying to buy around $60k (plenty for 38-42 feet of boat, perfect for 1-2 people) and saving the rest for upgrades.
The above is good advice.
With $60 k to spend and a Florida location ixnay the ferro.
Avoid teak decks. They make the boat hotter inside and need replacing at about 20 years at HUGE cost.
Budget for AC if you are going to live at a dock in Florida during the summer months.
If you are going to be living at a dock with the odd day sail you need not look for a boat with all the cruising stuff that costs money. RIB + 15 hp. Minimum of 3 anchors plus chain and rope. Electric anchor windlass. Solar panels Wind generators Big battery bank. Water maker. But if you are serious about cruising you need most of the above.
Go look at something like this Corbin CLICKY
Then compare it with a Beneteau CLICKY
Take a digital camera and take LOTS of pictures and notes. Start building up a list of things you like and hate.
Finally do not buy a wooden boat regardless of how cheap it is.