There has been some posts here where folks have tried it but I'm not sure how long it lasts and as Jay J said, it could be every few years just like everything else. People have also painted aluminum. Talk to your local paint store.
Avoiding painting and the high cost of painting is one of the main reasons people put on vinyl siding. If you don't like the color, you may be better off in the long run by replacing the siding. If you have a passion for painting all the time, then just remove the vinyl. Just my 2 cents.