I'd find a bone stock 1st gen that's in good condition and in someone's driveway for $500-$800. Then spend $4K and a lot of elbow grease doing it right.
edit: Though a free truck from a relative... also nice.
Back to the topic(in case anyone else is lurking of course)
I spent $600 on mine and everything worked.*
*Evrything major that is - needed new carpet, rear seats, a/c blower motor, new headlights, alternator and battery, windshield, brakes, and tires. Whew. Rest of it was in great shape. Engine was fine, A/C was a year and a half old(totally replaced with R134a system), had a working radio, new CV boots, 2 year old transfer case, and so on - it was this guy's daily driver. It ran fine - just looked like it needed mucho love. (had nice bull bars and nerfs on it as well)
Total spend was maybe $1500 on parts. Transmission went out 9 months later - just had it put in (MC).($1300 total, here) I've got $3500 into it so far including labor and the initial purchase. Everything but the trans and windshield I did myself. It's a very nice and solid truck. I joke that I could drive it to Alaska and back. I know it would make it with a few extra cans of gas in the back.
Note: Blower motor? Pay the shop to install it. Yikes what a PITA. Worse than the alternator swap. I think I lost an inch of skin off of my knuckles doing it.
I figure I could sell it for $2500-$3000 so that's what - less than $50 a month I lose if I sell in a year? Probably will put another $1000 in the next year into the suspension, a winch, plus various bits to make it decent off-road.
Moral: DIY if you're going to mod it or fix it.
