I agree with this article when it talks about one of the benefits of siding on a house being that you don't have to paint the outside of the house. A friend told me how much he had to pay to have his house repainted. I had no idea paint and labor would cost so much.
I was really pleased when we finally found a house after looking at close to 100 of them. I was also pleased that the house had vinyl siding because I thought this would mean there would be virtually no maintenance on the exterior of the house.
I worry that if I do decide to paint the vinyl then this will mean I will have to paint the siding again in a few years. I don't want to get into a cycle where I am painting my entire house every three to five years. If that's the case then I would rather have bought a house with wood siding.