I'm not sure what your skill level for painting is. If you don't have a spray gun, you could buy the spray cans. I have painted a bumper with spray cans before and have got excellent results.

I did this one a couple months ago and recently buffed it out and no it looks great.

I'll be going with spray cans because I don't have access to a spray gun, unfortunately.
As far as painting skill:

- Expert
- Good
- Fair
- Bad
- Me

The only things I've ever painted has been model rockets, so this is going to be interesting.

I really do not want to drive around without a bumper cover for weeks though, so I'm not sure what to do about that. (Is it even legal to?)

You can buff it out while it'* on the car. I would recommend taking it off to paint and wet sand.

Do not put wax on it until you've waited 3 weeks to a months. Wax will not allow the paint to breath right. Rubbing compound will not make a difference in terms of effecting the paint.

I'm not new to painting cars, I wouldn't call my self an expert or professional. I am very good at it.

I just had a look at the cover and there'* huge flakes of the paint gone down to the primer. Apparently the previous owner hit something and caused the cover to flex, breaking the paint right off. I might just buy a "new" bumper cover for $40 instead of trying to fill in the low spots. Pictures tomorrow.

If you see spider web cracks in the paint those will come back on the new paint. Only way to fix is to sand them down to the bare plastic and fill back in. Very time consuming and hard to do. I know. That'* why I pulled a black one that was in mint shape.

The more I look at that bumper, the worse it gets. I'm just going to go with a whole new cover. Apparently someone tired to fix the paint once and didn't bother masking the chrome. I'll take care of this bumper before I try to tackle the rust.

I can't blame you for not wanting to repaint over someone else paint job. It can make for a hard difficult job.

That black cover you see I got was in great shape. Black shows every body imperfection this one had none. It just needed to be sanded down and painted. It would take a bit of time to get those paint chips filled in.