Here's What I Did...
I started out looking for Catalina 22's. Even people who know little about sailing have heard of a Catalina 22.The criteria I had when I was looking for my first sloop-rigged boat last year was:-Easy to sail-Easy to transport so I could check out different lakes before settling on one (pretty hard to do with a fixed keel boat unless you have lots of $$ to burn) and we could take it on vacation to more distant lakes-Great parts availability-Great on-line community for advice-Enough space to enjoy staying on it for a weekend-Great re-sale-Less than $5K acquisition costI figured I'd buy a 22 then get something bigger in a couple of years when I'd gained more experience. As I was looking at boats, I found a 1985 MacGregor 25. I could see pretty quick what the difference was between 22 and 25 feet. It was well-equipped, very good price, and since I'm a tinkerer, still areas I could improve. Most people who talk about Mac's being crappy boats have never even set foot on one. Can't say I'm a huge fan of the "power sailor" 26X & M models they have been building for the last 12 years or so. Of course, I've not sailed one but I have talked to quite a few people who have and do own one. Anyone who has sailed on my boat has been impressed with the sailing manners, sailing well on all points of sail and speed. The 26D and 26S models, collectively referred to as 26C (classic) by reputation are good sailing boats and you might like the full rear berth better on a 26C than you would like the sleeping arrangements on an M-25.You may also find your first mate doesn't care to sail, but would rather be along for the ride. My wife enjoys our boat but isn't as passionate as I am about it, so basically even when she's along, I'm still single-handing. Get something you can single-hand in case you find yourself going alone or if your wife just enjoys kicking back and reading and doesn't want to be bothered with handling "those rope thingies".I've had the opportunity to sail a Hunter 260, 28.5, 31, and 33, Catalina 22 and 27, and Cal 25 and I have to say I'm never ashamed to go back to my Mac 25. I can find something I like better about each boat and something I like less vs. my own boat. Each boat has it's place. Until you get up into the fixed keel boats, you are going to find trade-offs. If you buy a boat which trailers and launches easily, it will be more tender than a fixed keel boat due to the nature of ballasting and likely won't have as much cabin space. If your goal is primarily day-sailing with occasional sleep-overs, a smaller boat will work for you. If you are dreaming of camping on the water for a few nights to a week, you'll want something bigger w/ full standing head-room.My opinion is the H-260 could be a good starter boat for someone who really wants space in a trailerable boat, but IMO, it doesn't sail as well as a C22 or M25. The pedestal wheel version is not a great single-hander for a newbie w/o auto-pilot. All the control lines, though led aft, are too far forward to stay at the helm to tack or jibe. As well, until you get going in a good wind, they seem to have a fair amount of side slip, pretty much the case with most centerboard boats w/o some sort of stub keel. I'm just not a huge fan of water-ballasted boats as of yet. The M26C's are water-ballasted FYI.The main annoyance I find on my 25 and what you will find on an M26C or any 22 foot boat is a lack of head room.A lot is going to depend on what you want to spend too. Since you are new to sailing, and don't know if you will even really enjoy it, start out with the goal of finding a cheap C-22 in good shape (there are a couple hundred for sale on line in any given week if you look up all the various on-line classifieds and individual marinas, just Google "Catalina 22 for sale") and go from there. Find someone who "has" to get rid of their boat. I don't have a problem being the beneficiary of other people's misfortune when it comes time for someone to have to sacrifice an asset to pay bills, move, or whatever.If your path leads you in a direction like I got led, so be it. Another reason to buy a trailerable boat first time around is fixed keel boats generally have a longer sales cycle because a prospective buyer has to add in transportation/rigging/etc. costs unless you live in a coastal area with lots of sail boats or the Great Lakes.Best of luck with it. Aside from the "stay away from MacGregor" comments I pretty much agree with all else said here.