Nancy,
Maybe our experiences over the past year and a half will be helpful to you. We're fairly new to sailing, and bought our first boat (other than a decrepit Sunfish with a waterlogged hull) about a year and a half ago.
We'd been dreaming for a few years and frequently stopping in at a local place that always had older used trailerable sailboats for sale, typically 22' Catalinas, Hunters, and O'Days from the 1970s. Our initial reaction was that we couldn't believe we could afford so much boat for under $3000! They weren't in bad shape although there were usually a few things that needed attending to, and most included an outboard and trailer. After doing a little digging around and sailing with a friend on a 30' S2, however, we decided to see what we could afford in a slightly larger boat.
We found two 26' Pearsons fairly close to us. One was about thirty minutes from our house, in the water on a smallish lake in a nice working marina with helpful people running the marina, with an asking price of $5000. The boat was very tired and needed a LOT of attention; soft spots in the decks, spider cracks every where, poorly done "customizations," and just generally very much "used." Still, it had a 15hp Merc on it and it was on the water sailing. We kept looking.
The other 26' Pearson was almost two hours away from us and it had been on the hard for maybe 5 years at a marina right on Lake Ontario. Asking price was also $5000. It looked to be in much better condition, and we had a good, very experienced friend with a beautiful boat in another marina only a could hundred yards away across the small bay. He came over, helped us look the boat over, and gave his OK... "This'll work. Offer him $1500." What? He's asking $5000! I didn't want to insult the owner, so I offered him $2500. He jumped at it like a starving dog jumps at a steak. I should have listened to my friend. At the time, I thought I had STOLEN this beautiful boat!
Here's what I've got into my almost free, stolen boat so far that I paid a paltry $2500 for. I've done ALL of the work myself. I shudder to think what the labor would have been.
Total rebuild of 8hp Johnson Sailmaster lower half - $250 in parts
New gas tank and hose - $75
New running rigging - $300
New sails - $2000 (main, working jib, 150% genoa)
New bulkheads, mast support crossbeam, and two compression posts - $300 worth of white oak (beam and posts) and Russian Birch plywood (bulkhead)... and a TON of time.
Rewiring of mast, including new deck and steaming combo light - $150
New battery - $90 (we've got a great "blemished" battery store near us; the same battery at West Marine was over $200).
That's all the stuff that was NEEDED, although we could have lived with the sails that were included with the boat. The jib was too small, as was the main, and they were both very badly stained and pretty much shot. The previous owner was nice enough to "throw in a genoa, too!" but it turned out the genoa was for a furling system (which we don't have) and in three tattered pieces. Great. How nice of him. We did sail it a few times on the old jib and main, and it was fine for learning. The new sails were more of a treat for us after all the hard work of getting it finally back on the water again.
There's a ton of other stuff that's more regular maintenance-related; epoxy supplies, bottom paint, compound, wax, etc. Basically, though, without the sails, we HAD to put over $1000 in parts and probably 40 hours of work into the boat. I'm not complaining; it was my responsibility as a buyer to be aware of that stuff. The fact that I missed a lot of it was my fault and I just consider it another lesson learned. Yeah, it would have been nice if the previous owner had been honest, but hey... unfortunately, not everyone is.
I'm still fixing leaky portlights and replacing the head, but other than that the major stuff is all set.
NOW.. here's why I'm writing. My original plan was to get this boat (about 2 hours away via highway, or 3 days away via Lake Ontario and canals) down to the small marina nearer to my house so I could work on it and use it frequently instead of making the two hour drive every time I wanted to sail or work on the boat. The quotes I got to move it were all over $1000, so I didn't. I probably should have, but my pea brain was still in the "I'm not paying almost half what I paid for the whole boat just to move the @#$# thing!" mode. Instead, it's still at the far away marina, and I haven't driven up to it NEARLY as much as I should.
In addition to the purchase price and additional parts, I've also spent about $2500 at the marina where it's located; two winter storages, one season's slip fees, shrink wrapping, stepping and unstepping the mast, one launch, and one haulout.
Sooo.. my $2500 steal-of-a-boat has cost me, not including labor, about $6500 so far, and I've owned it for a year and a half. Granted, it's going to get a little better now that the major stuff is pretty much fixed, but the "birth process" can be rough. The fact that the boat is not local to me really eats at me. The sailing and opportunities where it IS are much better and more plentiful. However, if I did move it here we'd be using it many times a week. Tough call.
Main points?
1. Location, location, location. Buy where you ARE, if at all possible. Boats in the range that you're looking at should be pretty plentiful most places. I may even have been better off buying the boat that I thought was a basket case just because it was here.
2. Triple the price of the boat in your mind, unless it's truly beautiful and very well kept up with great maintenance records. In that case, the price is probably already at least doubled anyway.
3. If going for a trailer sailer, make sure it has a trailer included and a good outboard. If you end up going for a keel boat, you'll need stands or a cradle. The cradle included with my boat, turns out, doesn't really fit my boat correctly and it's not adjustable. I'm STILL trying to figure out how to solve that.
Well.. that's enough for now, I guess. Take your time; you'll find the right boat. If it's far away but it's the right boat, factor in the price of getting it to where you want it and go for it.
Best to you.. good luck!
Barry