However, if I can spend a few hundred dollars on a "hangar paint job" to impress a larger field of prospective buyers... should I?
A few hundred dollars might buy you the paint. If you don't strip it and paint over the old, cracked paint, it will show, bad, for just what it is, a cheap paint job.
True, shine sells, no doubt about it. Unless the paint is alot worse than the pic looks, I'd consider a good compound and polish job, let the new buyer decide if he wants to spend five grand on a decent paint job.
Charles