How bad does this look?

I'm with the majority here. 2k is out of line. I wouldn't even give 1k for it myself. I've bought 2 rusty A-bodies each for 1000. but neither have the roof rusted thru. They were also more desirable models and run and drove but not well.
I think If you really like it 1000. would be a cheap car to drive if the drivetrains is as sound as you say. Im not a slant six fan myself. It would not be a car to fix up as a keeper in my opinion.
It could do the job for you till a better body came your way. And you could do the cheap body repairs on it so it would look decent as it got you around.
I remember how several of my first cars were not desirable by anyone not even me. But they got me around good till I found a better body to swap the parts into. They were new yorkers with 440s though. I personally would buy it as cheap as you can and use it for the disc brake swap on a 67- 72 model when you find the right deal.