I would like to hire a painting contractor to paint my apartment, but there are a few issues with the walls and I am wondering 1) if the painter would be the one to handle all of them or if not, who do I call, and 2) how would the painter/other repairperson fix these issues (so I know if he's going about it the right way or not). They are as follows:

1. Paint on wall edge right next to window openings has come off in large chunks (up to a few inches long) down to the bare wall in 3 or 4 spots. These areas must have been painted multiple times as the paint bits that came off are really thick. Should the bald spots be drywalled & primed to the level of existing paint?

2. Baseboards have been removed and in a few spots, took paint off with it. In a couple of these spots, the remaining paint has curled edges. Would the painter peel all this curled paint off until it stops coming off? I think ALOT may come off then, but if that's what has to be done, so be it.

3. I've been meaning to have the stair rail removed and a new one installed on the opposite wall. Removing the rail will leave big holes in the drywall. I can't imagine it's a painter's job to fix this as it's pretty major repair. Would the installers of the new rail be the ones to fix this drywall damage (for extra $)? But the order of things isn't quite right, as the drywall needs to be repaired before the paint job, but shouldn't the stair rail be installed after the paint job?

4. Other minor issues in drywall. My FIL applied joint compound/paint to fix some holes he made in the ceiling, but didn't sand them down well. I removed a couple stair rails in other areas & fixed the drywall & repainted, but it could look better.

5. This is kind of a separate question, but I also need to have baseboards installed. Should I get a separate contractor to take care of this, or are competent painter/baseboard installers pretty common?

Before anyone suggests that I take care of these issues myself, I am DIY'ed out! I installed the flooring in 80% of the apartment & most recently had to completely repaint the bathroom after the awful job the GC's guys did began to bubble within days of completion. I have many other minor repairs to do and it would be a huge weight off my shoulders knowing that the two biggest things left, the drywall+paint & baseboards, were going to be accomplished quickly and professionally. Your advice is much appreciated, as always.