I think you could find what you are looking for in that price range but I would worry about what the boat would need in the near future. Old boats can burn cash quick when outdrives are $4K each, motors $6K+ each and labor runs $50-80+/hour. I guess my point is when making a purchase like this look at the full picture about what it is really going to cost you.
You might consider a 22-26 ft boat with a single big block in that price range in excellent condition. As you get into the bigger boats prices for everything seem to go up exponentially. Fuel, insurance, storage (not an issue for you), bigger tow vehicle, accessories, etc. etc. I find it easy to spend $120 day with my boat (a 1989 Formula 242LS with single 454). This summer I'd spend $50 on fuel, $20 beverages/ice/snacks and $50 on lunch for two at the dockbar. Towards the end of the summer, the $50/day didn't buy much gas and we didn't go far. Worth every penny but this daily expense adds up quick. And that's before repairs, maintenance, etc. Wtih two motors you can double gas and maintenance costs. To estimate fuel usage, look at gallons per hour per motor. Multiply that by the price of fuel. Toward the end of the summer (when gas was $3.50 on the water) I was looking at $30/hour at cruising speed. Seems to me a 27-32 boat with big blocks would be $60/hour or more (right?). When you are burning gas at that rate the boat payments are easy.
Now the good news. You are in a buyers market. I've had my boat for sale for months, no takers at $13.5K and it's in nice shape...here is a gratuitous picture. Searching boattrader I've seen a couple 242Ls in the midwest.
Good luck with your search.