Thanks everyone for your recommendations and help.
Sumner, I bookmarked your site and will use it as a future reference. Lots of good stuff there.
The seller of the eBay MacGregor 26s pulled the original listing, and
relisted it with an unknown reserve. It's at $1525 now, and hasn't met the reserve price. I'll pass on that one.
I looked at the
Tangerine 18 yesterday, and wasn't impressed. I like projects, I like working on boats, and I do everything in my power to save stuff from the landfill. But between the condition it was in (multiple, large soft spots on deck, all exterior wood (incl rudder) needs to be replaced) and the cheesy design, I think this one should be scrapped. I've read elsewhere that the price of an older trailer sailer should approximate the worth of the trailer, sails, and outboard, with the boat being free. I'd agree with that statement, and think it applies here (a 5hp outboard was included). The seating area of cockpit was abnormally small (4'?) due to the forward rake of the companionway (which itself is a hole to crawl through to get to the cabin).
Looking is fun though, and that's why we spend the effort on looking at different boats - to see what we like and don't like. Myself, I want a sliding hatch above the companionway.
For the past few years, I've been planning on building a teardrop style or gypsy wagon camper for my family, and have a ton of design ideas for convertible sleeping and storage areas, kitchen, etc. Could I implement those ideas
into a boat that needs its interior rebuilt? A cabin rebuild has certainly been done before, (
link) and doesn't look too hard. The Cal 21 has a swing keel, and some odd design quirks though (detachable keel cable, removable cap for when it's deployed). However, it's a 21-footer that weighs 1100 lbs (360lb keel). Lots of room, and I could tow it with anything. I'll pass this time, but maybe if it was local....
I guess what I'm heading toward is a stable, floating camper that's lightweight and easy to tow and launch. Something along the lines of author
Larry Brown's philosophy:
"Let me share with you a fairly well-kept secret. It's so often true we could almost call it a law:
The use a boat gets is in inverse proportion to its size and cost"...."
Think minimum. Buy something that costs less than you can afford. Accept the challenge. Find ways to make due." (from "Frugal Yachting", "Part I: The Invitation").
That, and the fact that no boat is ever "big enough"; everyone eventually has "two-foot-itis" and wants something larger (until they realize it's too big to use easily or too expensive to maintain). I've owned larger power boats and learned this lesson myself.
Maybe something will come around this fall/winter, when the market's more depressed and prices lower. I can spend the winter getting her ready for next year.
You can't get any cheaper than FREE though!
https://www.free-boat.com/free/26-grampian-port-orange-fl/?lang=en (not really trailerable though due to keel)
https://www.free-boat.com/free/westerly-25-twin-keel-boat-kinsale-va/?lang=en (sorta trailerable, but too heavy for me)
(Yes, I know the "free" boat is also the most expensive, in the long run. It's just fun to look though.)
Anyhow, enough rambling! Back to work!
A swing keel boat will be heavier than a water ballasted boat. 
