Okay so I'm slowly closing in on what I'm looking for. Sounds like a tiller will definitely be far more conducive to a good learning experience for a newbie like myself. I'm to be on the lookout for delaminated decks, tabbing coming loose, old standing rigging (10 yrs or so?), and old sails. Having a good set of sails in the package will be a definite plus as I looked up some prices using a Catalina 25 as a reference point and discovered I'd be looking at a 2.5 to 3k expediture, if not more. Also that I shouldn't be overly concerned with the race history of a boat, as it may have more wear and tear, but will generally be better maintained. I already know to look for an outboard (and preferably a diesel OB) rather than an I/O motor because they are easier to maintain and repair on the fly.
Sailormon- I maintain that weight won't be much of an issue (I have a late model F-250 SD w/ towing package to include trailer-brake system. It's towing cap. is in the neighborhood of 16k lbs. It's light on creature comforts but it's a brute built for hauling.) and if a bigger boat generally sails better than a bigger boat is what I should be on the lookout for. The added cabin space will make it worth my while for the occasional weekender. Besides, the rigging which an experienced sailor finds tedious will all be new to me, at least for a while. If I was in a big hurry, I'd just get another powerboat. None the less, I will consider myself warned.
I should also note that I'm not looking for "the" boat. Just a boat I can learn to sail on and have some fun in the process. If I really catch the bug, I'll upgrade to a bigger, newer boat a few seasons down the road.
All that said, I've been doing some more research, and of course, I have more questions.
Of a centerboard or a daggerboard, which is "better"? (I'm leaning towards centerboard, due to it's ability to fold if I find myself grounded) Or should I look instead for something with a fin keel? Do they make boats with fin keels that are float-on trailerable?
I keep hearing that due to the low cost and high availability a Catalina would be a good choice for me, but I've read that the quality of the brand is not all that great. I know on my budget my choices are limited, but would an older Catalina be able to stand up to some rough handling? Not that I intend to be rough on the boat, but I am after all new to this. I just would like to know that the first time I bump a stump or manage to ground myself I have a pretty good chance of sailing away from it, rather than swimming for shore because the hull caved like an eggshell. On a side note, are all monohull sailboats self-righting to a degree, or is that particular blessing reserved for full, weighted keel boats?
And one more, although it may be one for the learning to sail topic: How much effect would hiking have on a boat in the 25' range without a full keel? I may occasionally have a few friends aboard, but most of the time it'll be just me, and I don't have that much weight to throw around.
Once again, I've prattled on for far too long. Sorry about that, and thanks for bearing with me. I have so much to learn before I can make an educated purchase. Good thing I still have some time before I can even look at another boat. Not really a good thing though. The desert sucks. I'd rather be paddling a canoe through a mudhole.