I've got an 88' hatch, black and silver, with some of the usual surface rust on the doors and a little surface rust on the roof.

I want to getting it looking nice, but have never painted a car myself, and probably won't have the time to really dedicate to it in one weekend to do it right. Plus, I would have to paint it outside. I did a little "learning" on the passenger door a few weeks ago with a rattle can. so so...

What type of prices should I expect when approaching different shops to paint it for me?

I will either go all black with a gloss finish, flat black everyting, or silver (a lighter choice). Leaning toward flat black.

Any suggestions or feedback?

 

How much you pay depends on what you want. A GOOD paint job is going to run you around 2K or better. You can get a cheap paint job, but if you get a 200 buck paint job, you will have a 200 buck paint job.