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That is a personal pefrence question. What works for me might not do it for you. Also, it depends on the deal you get. For this budget, if you have the time and energy, I would look for a great deal this fall and winter in Florida. Right now the sunshine state is loaded with a glut of used boats. Many are having problems getting insurance for boats and want to unload them. I know of several guys that have made the trip to Florida to get a great deal on a boat and bring it up north. Look around, you will find what you like.
With fuel near 4 bucks per gallon, you might consider something with a diesel that is a little slower too. Some ballpark numbers to think about:
A 32' CC with twin 300's burns 35gals/hour at cruise. A 27' CC with twin 225's burns about 20 gals/hour (or more) at cruise. A 23'er with a single burns about 12-14 at cruise. A 21'er with a 140 will burn around 8 or 9/hour. A 27' single diesel is in the 5 gal per hour area with a slightly slower crusise but about 3-5X the life of a OB. (I know there are exceptions to all these but this is about the norm)
My only advice is to avoid gas inboards, you will reget it and convert. I think a lot more boats will be on the market this winter. People are fet up with fuel costs. (The guy at the gas pump told me he is selling a lot less fuel this season)
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