Stained vs. painted wood

I have read all sorts of articles and blogs about the debate between painting over wood that is stained. Depending on who you ask it's either the greatest sin you can commit in a old house with any historic character, or the best thing you can do to brighten and clean up a room. Of course there's a lot going on in between these two extremes. When we moved into this house, the trim upstairs had already been painted white. The doors upstairs were still unpainted wood but had been stained super dark. Everything downstairs except the kitchen had been left as stained wood, sort of a deep rusted hue. It's pretty, but also pretty beat up. Chips out of the wood, nails randomly in the wood, etc.
Andy belongs to the camp of don't ever paint the original wood. When I proposed we paint the upstairs doors to match the trim that was white and to brighten things up he protested but reluctantly agreed. That turned out to be quite a project, but we have most of the doors at least primed white and even with that I think it already looks better. He does too. Sometimes I wish the downstairs had been already painted white before we got here too. I can't bring myself to paint over it. It really is sort of charming, but damn if I don't like me some white trim. It makes picking paint colors so much easier. It makes everything brighter and feel more open. Andy says he likes the cave feel. While I sit here and try and think of paint colors that can brighten up a dark wood stain, he talks about making it feel darker. See, he's a "Rustic/Lodge" decorating style, while I am a "Nantucket Beach" style. The quiz we took made it clear that my bright, light colored fantasies are exactly what he is NOT looking for. I guess we'll have to make up for it in other ways. But in all seriousness, has anyone ever really regretted painting wood trim white?