Replace the vinyl with vinyl. It will look better in the long run. Some of the newer products aren't bad.

OP here, thanks for all the feedback.It's greatly appreciated.

Will you also need to repair the brick mortar? It needs to be touched up every so often too, to avoid leaks.

Definitely hire someone who specializes in siding/roofing. They will be able to quote you on the trim replacement, too, plus identify other areas that need to be repaired. Get at least 3 separate evaluations/quotes and DO NOT pay for this up front. Ask them to look at your house and give you a bid for whatever painting and repairs need to be done on the exterior. Make sure they are doing all the work themselves and not subbing it out (i.e. hiring some day laborer to do the painting). Ask for and check references.

Also, drive around and look for active work in your area. Contractors will post signs during/after their work and you can take a look first hand (and stop by after hours to get feedback from the residents).

No, the painter will usually not do that. You should look for someone who does siding repair work. Get that done first and then have the painters come after the siding has been repaired. If you have any DIY skills, you can take a look on-line. I believe that "This Old House" has some videos about how to repair siding. You might be able to do some of it yourself. If you aren't comfortable doing it yourself and don't have any other recommendations, you can go to http://www.fixthehome.com/siding/repair/ and find some contractors to come out and give you an estimate.

Just a word for the vinyl siding: try to avoid painting it using a darker color -- heat will make vinyl buckle. There are paints specifically made for painting vinyl a darker tone -- example: sherwin williams "vinly safe" technology. Do research on that before choosing a darker tone.

We have a house with combination vinyl siding and brick, with wood trim around the doors and windows. We are WAY overdue for painting, and there is alot of rotted wood that will need replacing. Will a regular house painter replace/repair the trim and do the painting?
Or do I need some other type of contractor?

Also, anyone have experience with getting vinyl siding painted? I've talked with people who had aluminum siding painted and were very happy with it.
Thanks in advance!