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Can vinyl siding be painted or stained, and more importantly, does it last or will I be repainting every year like a wood sided house?

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Yes, you can paint it. Make sure you clean it very well (use a TSP Cleaner) and then use a primer first (although some sites say you can get away without a primer).

Also make sure to paint it a lighter color than the current one:

I assume you're painting with a lighter color paint - vinyl siding painted a dark color can have problems with warping and expansion in direct sun.

from http://newsgroups.derkeiler.com/Archive/Alt/alt.home.repair/2008-08/msg03475.html

The expected life of the paint job will be dependent on the weather conditions for that area of the house and probably be about the same as a wood sided area.

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