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!

Cheap nasty builder grade MDF could run you a couple of thousand. Great looking, complex compound profiles, in wood, could run tens of thousands. The labor will be the biggest bite out of the job. It takes a good amount of skill to do correctly, and not look like someone slapped it up with their feet. This isn't a place for the $1.98 Craigslist special handyman.

Hi, Johnny-- For your currently maroon room, I'd split it up in a few ways: Base, window and door trim to new white in updated palette (semigloss) Walls to your new grey in updated palette Keep overhead beams in current tone, but paint out the v-groove between beams in your new white (flat) Should add light to the space, highlight the roof architecture, and set off your updated flooring in there. One thing I noticed from your fireplace photo is that your wainscot paneling dies into one side of the fireplace and doesn't run that whole wall. That seems an odd place to end the run, so I'd consider having it run at least into the next corner or wrap that room, as well. Let us know how it all turns out - and keep on!

Thank you! Hiring a professional has been hard to find since we need it down in a few weeks so I guess we will have to try out on some test trim to see what works best as you shared with brush and roller. I heard about a adding agent to paint to that could help eliminate strike lines or texture but not sure how well it works.