It's tough to say how much you'll be looking at to restore to a good driveable, useable condition. I'm not sure how much an engine and tranny rebuild would be, but I'd say you're definitely looking at around $1500-2000 bucks if you can't do any of the work yourself. If you plan on getting it painted I'd let the person that paints it probably fix the tailgate problem. If it isn't a structural problem with the body the problem might show up when the tailgate is dissassembled to be painted. You can spend what you want with the truck for paint. $1000-$5000 depending on the shape of the body. It's tough to get a good paintjob these days on an older vehicle. I'd say if the body isn't rough you could get new paint for 2K. There's a ton of variables though........Tires...wheels.....interior.....I'm in the same situation as you....my grandfather bought mine in '76....then my dad had it in '85 'til he died in '99....I got it from my mom in 2002 and I've been working on it pretty hard and heavy since last year and I've dropped about $4K or more in everything...it's starting to come together. I wouldn't sell it for any amount of money. Like you said, it's probably one of the only physical things that you have left, and you can have a part of him live on with you.