You will, no doubt, get as many opinions as posters! Different people will like different types of
boat. Me; I like deep fin
keel,
single masted boats fibreglass. The next guy might like long keel, 2 masted
steel boats. Ain't none of us particularly right nor wrong. It is important to find a style of boat that works for you.
There is always a temptation to buy as large a boat as you can afford, but realistically, unless you are particularly wealthy, it is better to buy as small a boat as you can live on in comfort. For me, I chose 40-foot, but with hindsight, I might have been better with 38. The cost of running and maintaining a boat seems to be proportional to the length squared (i.e. a 50' boat costs 4 times as much as a 25'). Also, if there is only going to be 2 of you, handling a large boat in and out of
marinas can be a real handful, especially if you are (a) not particularly experienced, and (b) don't have bow thrusters. You also don't want a boat whose
sails are so big and heavy that you struggle to hoist them and handle them. Remember also, that
insurance, slipping
fees, berthing
fees etc will probably all increase with the size of the boat.
Phone a
sailmaker and ask for a quote for a new
mainsail for a 30' boat and for a 40' boat... you might get a surprise at the difference.
You are going to lean more from your
surveyor than you are from us. Ask around, and try and get recommendations for a good/repsected
surveyor (don't, as a
rule, use a surveyor recommended by the seller - there may be a conflict of interest). Listen carefully to your surveyor. Make sure that, when you get serious about a particular boat, you arrange to get it hauled out of the
water, so the
hull can be inspected, particularly since the boats you are looking at are in the 25+ years old bracket. If the basic systems (hull, keel,
deck,
engine,
mast & standing rigging) are in good condition, you can always fix the small things. If there is a problem with any of the major systems, you are probably looking at major expense to fix.
If you
live aboard, you are going to spend a lot more time at
anchor / on a buoy / in a marina berth than you are actually sailing... comfort may be a more important factor than sailing performance.
Finally, don't get too worried about finding "the perfect boat"... it doesn't exist. Even if you had a
budget of 10 million bucks, it still wouldn't exist, and with a limited
budget, you just have to find something that is good enough and fix what you can and learn to love what you can't. In the end, it doesn't matter whether you buy a
sloop,
ketch or yawl, fibreglass,
steel, aluminium or
ferro, deep keel or shallow, etc. Each has their advantages and disadvantages. If one was inherently better, we would all be sailing identical boats. If you want to do it, you will, and will have fun despite / because of the individual strengths, weaknesses and idiosyncrasies of your vessel of choice. Don't worry too much.