One of your key points were "winter vehicle". With that, I would put as little time, effort, and money into the body as possible. Simply because, even if you make it 100% new and protect it the best you can, the road salt will still eat it up.
Take the black one, spend a bit to get it roadworthy, maybe fix some of the rust, swap in a clean interior to make it comfortable, then enjoy it. Maybe get a good 5 years out of it, longer if you continually treat the underside with a good oily coating every year. You will have a decent truck that you didn't spend a fortune on and you can actually use without fear of dents, scratches, dirty dog feet, winter abuse, etc...
That would be my take on this situation.
Take the black one, spend a bit to get it roadworthy, maybe fix some of the rust, swap in a clean interior to make it comfortable, then enjoy it. Maybe get a good 5 years out of it, longer if you continually treat the underside with a good oily coating every year. You will have a decent truck that you didn't spend a fortune on and you can actually use without fear of dents, scratches, dirty dog feet, winter abuse, etc...
That would be my take on this situation.
