Update.... My brother is actually a mechanic and opened his own shop (and dealership) a couple weeks but they usually turn quicker jobs. The person/shop they outsource major jobs to said it would cost $200 in labor and I can pickp the parts on my brother's dealer acounts at napa or advance. They are closer so I may just go this route, as I feel a lot safer changing the oil and running it 8 miles than making a 40 mile trip or having to rent a trailer or have it flat bedded.

I have no idea if its the head gasket, I just assumed it was the most likely source. This is where you would start anyways right, looking at head gasket and head?

To answer the other question, I guess it depends on what the line is on overheating. When I got the car it ran up to ~230deg (?), its hard to remember, I think it got up to 215-220 and I got scared and cut it off, then it ran up higher sitting. It had a 195 thermostat, a reverse rotation fan, and some small coolent links, it would stay at 195 on the highway but heat up in traffic. I put in a 160 thermostat, a regular flex fan, and got the coolent pressureized correctly.

I'm not sure if this helps but I think it may have lost coolent into the engine while the car was sitting overwinter. I pretty regularly check the level and I'm fairly sure it would have been full when I was driving it last summer. First time I cranked it up this spring I had to add a inch or two.