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Personally I wouldn't stain or paint over wood trims, even though Oak is not as desirable as other wood species. I think we can always find a style that can work with Oak and be contemporary as well.
With out a pic of your situation it is really hard to tell what do do. But having the practical side of me come out this is my best advise!
Painting is a lot of work especially once the trim has been installed! Maybe taking it out and putting in an pre primed MDF product that can be sprayed and then installed would be better. I would use the oak moldings in a summer cottage or sell in a sale or give to a freind or family member. Painting oak just reminds me of refinishing something again. "Alot of WORK"
Happy Stripping!!
Debrasays
Hello Countrynlovinit,
Whether or not to paint woodwork is a common decorating dilemma. You might find this article helpful for making the final decision: http://www.houseandhome.com/design/wood-trim-paint-or-not-paint.
Of course, if the wood is in bad shape, it will probably look much nicer painted out regardless.
Hope this helps,
Jennifer
Web promotions editor
If you can post pictures, it would be a great help. I shudder when people talk about painting over good wood, but alot of times it does look better when it is all done. Not sure what all you are considering painting. Trim? Windows? Doors? Pics would help.