I just fielded a great question (the customer was actually referred to us by another paint store!) - in a 1950's house, is it better to strip and refinish the base trim or repaint it?
While there is never a one-size-fits-all answer when it comes to aesthetics, the caller had some interesting value choices to ponder.
Would the trim be worth the effort of stripping? Being a 1950's era house, the trim is most likely Mahogany, but not that cheapie 1970's Mahogany we are still trying to erase from memory.
How would the caller determine if it's the good stuff? Remove a piece of trim from as inconspicuous an area as possible, and see what's under five decades of paint. If it's good quality wood, then the choice can be made to remove the paint layers and refinish. If not, no harm done - re-install the trim, patch the wall if needed and repaint.
When it comes to the 'look', which is better? In this case, I'd suggest stripping and refinishing because the caller is painting his walls a pale white. This means the exposed wood trim will add some architectural detailing to a potentially very plain room.
If painting is the option, I suggest a color that adds some depth and richness to the trim. Perhaps a rich mushroom color or even a velvety cream - anything to add some interest without becoming distracting. In very few instances should trim become the room's focal point, but it can go far to add character and interest.