Originally Posted by Martness
.... Here are a few that are for sale nearby that I'm looking at: Morgan 382, 38 feet, yr 1978. A 1999 Beneteau 411, 42 ft long. A pearson 365, and a hunter 3800. Feel free to suggest other boats.
Very different boats from very different era's that will have very different issues. Two thoughts: don't be in a rush to buy anything. Spend plenty of time looking at A LOT of boats in your budget. (By the way, what is your budget? Remember that you'll need the cost of your boat + about 20% at a minimum to upgrade/equip and address basic maintenance issues)
Rushing into a purchase can lead to very expensive buyer's remorse. Don't forget to add up the costs of moorage, potential new sails, etc....
Read up. There are a lot of books that will provide a baseline for thoughts about design, etc... There are many boats that will do the job you're looking for. The trick is to know enough to be able to make a list of 8-10 models that are close to what you're looking for, then find the best boat for the money that happens to be on the market in your purchasing time frame... While your looking, take your basic sailing lessons (ASA 101-104, etc...) including some dingy time if possible.
Three books for you:
Yacht Design According to Perry: My Boats and What Shaped Them by Robert Perry
The Voyager's Handbook: The Essential Guide to Blue Water Cruising by Beth A. Leonard
Boatowner's Mechanical and Electrical Manual: How to Maintain, Repair, and Improve Your Boat's Essential Systems by Nigel Calder
I'm sure other's will pipe in with book suggestions. As you sail locally, read, etc... you'll meet people and get a much better idea who you might look for to help skipper your boat.