Oh and Tyler I was looking back over your numbers there listed. Where are you from wher a paint job cost $5,000 dollars? I am sure they do, but here is my philosophy. I do the paint myself. Independent? smart, and who says I cant paint better than the pros. Its not that hard to figure things out when your are broke.
You cannot paint the car yourself properly unless you happen to have a very expensive spray gun and booth to keep all the dust out, and allow fresh paint to bake. Using a spray can will only make the car less valuable.
Once you get the car running, I would suggest driving around town to local body shops to get estimates. I bet you'll get anywhere from $3000-$10,000. Its all over the place. It is a very time consuming, labor intensive job. If you went with a maaco store, it would still cost $1000, and probably come out looking like crap.
What can save you quite a bit of money, and if you have time and patience, is to do the prep work yourself. You can remove all the trim, sand the car down, do any body repair needed, then send to the pros for paint. From your description, it would take a full 40 hour week to do correctly.
This is not something I would suggest if you don't have a garage or the proper tools to do. I think your best bet is to get the car running the best you can on your limited budget, then sell. There's really not alot of money to be made in the older benzes, especially restoration projects like these.
By the way, is this car titled in your name? You do realize that curbing titles is illegal, and you could face stiff fines if caught?