With all due respect to GJ's Follow-up, if you go through with this, you're turing a maintenance-free exterior into one that now requires maintenance. If you're gonna do it, I hope you go with a neutral color like white, baige, tan, bone, gray, or the like. You'll have to clean the siding first, and a powerwashing with just water isn't sufficient. Vinyl isn't like wood; it doesn't absorbe ANYTHING. The paint only 'adheres' to the siding.
Well, 'nough said. You ought to price what it would cost to have the siding replaced. When you get a price, then ask how much you can save if you do the demolition yourself. (You'll have to work with the contractor on this, and possibly do a side at a time because you want to minimize exposing walls to the rain. Use vacation days?) If you go this route, post up a new post or e-mail me directly with any questions. My best to ya and hope this helps.