As others have said, vinyl is almost maintenance free. I would opt for that rather than occasional painting.
If you are handy and have the time, It is not a hard job to do unless you have a two story home, that would cause additional concerns.
If you do take on the job, watch a lot of Youtube videos! Attaching the siding is the easy part and only has a few things to be concerned about. Leave the fasteners loose enough, so the siding can expand and contract and make sure any ends you cut allow for that expansion. I used siding screws to help control depth, nails will work, it is just harder to control how far the go in. A magnetic screw driver bit to fit your cordless drill is very helpful, when you are trying to hold the siding and drive the screw in at the same time. Find the direction you will most often see the house, have the closest piece to you over lap the next piece. The joint line is much less visible that way.
The trim work is where the thinking comes into play. It is not hard and after a couple of practice pieces you get a feel for how to cut the piece you want to install.
Vinyl will crack (especially when colder) if hit with a weed whip, or rock, so do purchase a few extra pieces and store it for a color match.