Mike,
I'm walking down the same road you want to take. Never had a Deuce, have limited mechanical skills and knowledge, and want a truck that runs. I checked the internet to get an idea of what's out there, compared prices for trucks and prices for parts and eventually came to the conclusion that I'll probably be better off spending a few bucks more on a truck from a reputable dealer who checks the vehicles he sells thoroughly and replaces, or repairs what needs attention. Dealers need to make a profit and will charge more than you may pay at auction. On the other hand, you won't have to pay a wrecker to pull you to a garage when you break down, and you know your truck will run. That has a value to me, too.
I found three dealers relatively close to me and contacted all of them. One, it turns out, only deals in parts, not in complete trucks. I visited one and was disappointed in the "salesman's" lack of product knowledge. Heck, if I know more than the seller, the seller really doesn't know much. I plan to see the third one this weekend. I already talked to him on the phone a few times and go there with the expectation that he will show me what he has and answer any additional questions I may come with while I'm there.
I suggest you check this site, Ebay, Craig's List and the internet in general for "for sale" ads from your neck of the woods. I've learned quite a bit from reading the descriptions, and by talking to people. Download the manuals from this site. They will give you a good idea what to expect in maintenance work.
I hope you find some of this helpful.
Jeff in Pennsylvania