$2000 isn't very much for body prep, and paintwork. So you will get what you pay for.

As far as the dents go I'd say how many dents are we talking about and how bad? What does "a tad" mean to you? Words have slightly different meanings to different people.

10 years ago I paid ca. $800 for straightening a fender that had gotten bent, bodywork, and painting it to match the rest of the car (that escaped the soft collision with a light pole)

I thought I got out pretty easy from that one.

I think you are being unreasonable on the time as well. Create a triangle, and put the words Inexpensive, Fast, Quality, one in each corner. You can now choose two of those, any two, and you will sacrifice the third. General rule of projects, you can never get all three at the same time. Doesn't happen.

If you don't want to pay him, and you want it done semi-well, you can expect it to go slow. If you want it done semi-well (or better) and fast, you'll have to pay up (either with him or someone else). If you want to pay a low price, and get it fast, one will simply spray over dirt and whatever else there is on the body.

Pick your poison.