I don't think this would look funny at all, but then again, it is exactly when we did. ;-) The windows and doors are stained. The floors will have a natural finish. The baseboards and casing are painted white. I'm sorry we are still under construction, so I don't have great pictures. The doors aren't hung yet, but these might give you an idea. The ones "under construction" are our house. The finished pictures are some inspiration pics. Good luck! Our house "in progress". In this picture we combined stained stairs and windows with painted trim and window casing This isn't a great shot, but it does show the transition between the stain and paint on the windows. This is the only decent picture I have that shows a door (french in this case, but all the interior doors in the house are stained but not hung yet.) This door isn't hung yet (just resting there) but it give you an idea of the nice contrast between the doors and the trim. Inspiration pictures

1. I've included a link so you have a visual of dark baseboards and painted window trim. I see no reason you can't paint only the window trim. If you decided to paint the baseboards then I'd go ahead and paint the door trim also. My house is all white trim & baseboards with stained pine doors so I know how great the look is! :~). 2. Your doors and trim may only need a good cleaning, a touch up with stain and then sealed. Replacing will be much more expensive and labor intensive than just painting. If you decide to paint them, talk to someone at a paint store (not a big box) and ask about the products they now have that you can use instead of sanding. If the surface has really shiny finish then you'll probably need to do some light sanding. Here is a link that might be useful: white trim, dark baseboards

I've also painted old stained trim with no regrets. I did not strip it all (tried at first, but it was very aged and too difficult even with chemical strippers and heat guns!)- I simply sanded and used high quality Ben Moore primer and paint with excellent results. I personally much prefer white-painted trim to stained, UNLESS the house is of unusually high build quality. I come from a family of architects so am probably a bit overly-sensitive to proportion and design, so YMMV... but I feel like stained trim really calls attention to each element: doors, windows, baseboards, crown moldings are all brought into high contrast with stain and their placement and proportions become important design elements in a room. If they were well and thoughfully designed originally, that can be a beautiful thing. If not -I'd paint them. Our last house was a 1926 Foursquare. it was definitely much better built than most homes today, however, it was probably a Sears kit house originally, basically a builder-home from that era. i.e. not architect-designed like the previous Victorian I'd lived in. It had stained fir trim (with nice details) throughout, and DH and our friends thought I was crazy to paint it. Guess what? The house looked SOOO much better after I did. It actually became a much classier-looking house. The dark wood around doors and windows -which had been placed pragmatically rather than for aesthetics- made the house seem a bit akward. The white paint allowed the really GREAT elements in the house, like it's gorgeous birch floors, ample sunlight and great "flow", to really shine. Just my 2 cents!

The problem with doing touch ups or partially doing an area, is that it tends to make everything else dingy. From the standpoint of labor, it is also disproportionately labor intensive. You still have to protect the whole room, even if you decide not to do the ceilings, for example. Similarly, it is far easier and time efficient to do the woodwork before the walls, whether spraying or brushing the woodwork. Were I trying to save money, I would opt to do one or two rooms completely, rather than to do the whole house incompletely.