does anyone have a rough idea of how much it would cost to re-paint a 1994 short box regular cab s10

 

depends on how much body work they have to do to prep it before paint.
Also the door jambs usually cost a little extra too.
You can get a cheap paint job from Mayco for about $299 and up but they do not prep it.
Just take it in to a local body shop and get a quote.