If you like the look of the natural wood, go for it. I don't think it will look silly with the medium brown maple cabinets, the differences in stain/no stain will look great together.

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!

Have you seen Elizpiz's kitchen? It might give you some inspiration on what to paint and what to stain. There's something about your elevations that make me think of her beautiful kitchen. Here is a link that might be useful: Elizpiz's finished kitchen GW reveal

I"ve been staining wood a very long time. Don't tell me gel stains don't penetrate and that you should do 4 coats. you are not supposed to do 4 coats. gel stains do get lightly absorbed into the wood with also sitting on the surface. But It's not nail polish christinero. GF has enough pigments to 'stain' the wood w/one coat. putting on additional coats results in a tacky, gummy finish, and could also result in cabinets w/a poor finish, especially for a kitchen. this is from GF website on applying gel stain: Optional: apply a second coat to deepen the color. Apply no more than 2 coats https://generalfinishes.com/wood-finishes-retail/oil-based-wood-stains-sealers/oil-based-gel-stains I have worked w/ GF stains on many, many wood projects. one coat is fine. Like I said, if you want a darker color, then go with a darker shade. there is no need to do 4 coats! good lord. why create more work for yourself? Gel stains act more like a paint and tend to hide the grain of the wood. I would never use a gel stain on a beautiful piece of walnut, tiger oak or bridseye maple. it would cover the beautiful wood details. If you want to use 3-4 coats of a gel stain, then you might as well use an espresso paint. you will get similar results with a lot less work. you will need at least 3 coats of a clear top coat after the stain dries. please read the above link for the complete how-to's in staining your cabs. especially this part Preparation for Projects with an Existing Finish and Christinero,,,,,there are dyes, stains and gels. all three penetrate, but at different levels. gels are the lightest and don't bring out the depth of the wood grain like the stain or even the dye would. (I've used all three). but gel stains still penetrate. gels have a heavier ratio of pigments and tend to give off more even looking coloring.