Paintjob worth it?
 

I have a 1992 C1500
Auto 2x4 305 5.0L
105,000 original miles w original engine/trans
Reg cab w/ 8' box and good canopy
2 sets good tires

Basically, I want to sell my truck and hopefully upgrade (always drove Chevy, going to stick with Chevy)... and I'm wondering, will taking it in for a basic paint job help my re-sale or if it's not even worth it? The factory red is peeling pretty bad, primer and silver paint's in great shape.

I bought it for $1000 and have put about $800 into various fuel delivery, ignition, sensors etc. Replaced them all myself (at $100/hr, a shop's not worth it!)

Going to change the head gasket and exhaust (Cat if it needs it) and get it running strong again. Including all gaskets, bolts, belts etc that's another $400-ish

A paint job to freshen it up won't hurt unless you're going with a dirt cheap paintjob. The problem with a cheap paint job is just that, it's cheap. If you're going with Maaco, spend a bit more and you'll be a lot happier in the long run and improve the value on resale.

I've painted and restored a lot of cars over the years and one thing you won't get lowballed on in resale is a decent paint job. It's easy to justify and saves the new buyer from having it done.

I would say yes, the truck would be worth the investment as long as the truck isn't rusted out badly. Personally, all the things you've mentioned are things that I would want in a truck if I were buying one. You can probably have it re-clear coated to fix the pealing, and save yourself some money and keep the factory paint, which doesn't sound too bad.

Honestly speaking, an older truck that's had lots of work done to it, and still has a good frame and body is a better re-sell than a less fixed up newish truck. But I live in Michigan, and old trucks are rare to find in good shape around here. Mine, for example, is missing probably close to 20% of it's passenger side front fender due to rust. My truck has no resale value because of rust damages. If you can swing it, go for it and buy yourself a nice 4x4 new truck with your payoff.

Good luck