I remember the craze, in the 1980s, to strip every old piece of furniture to "expose the beautiful wood grain." And you'd see pieces in the antiques shows/shops with these crazy grains, mismatched woods, etc. My mom always said, "the guy who made this would be beside himself to see his ingenious usage of scrap wood exposed like this. If he thought you were going to stain it, he'd have at least made sure to use the same species of wood, and he'd have hidden the crazy grain on the shelf or in the back." Oh yes! & I, personally, think the appearance of old wood rarely benefits from application of poly. When I rebuilt a pantry window (1913 house) I found the casing was painted quarter-sawn oak. I'm sure it was always painted - and that much of the house was trimmed with scrap wood. That window remains uncased while I do other things. I haven't uncovered the other casing to confirm my scrap-wood theory. If it's not all nice 1/4-sawn I'll find somewhere else to use that and put something new (paintable) on the window. My first experience stripping paint was in the 1950's, as a child. My mother had an impulse to strip all the oak woodwork in her 1911 house and, as always, enlisted the passel of kids to help. We used stryp-eze - the harshest stuff almost - and no masks or gloves. We did a staircase, 8-10 double hung windows, some doorways. It's not something I would recommend, obviously, the use of the kids (or stryp-eze) but it's an indication that stripping paint is not rocket science. In her next house mom stripped '30's era "blonding" from a whole lot more oak woodwork, without help from any kids but this time she wore gloves and used a LYE solution & a WIRE BRUSH. (Blonding involves grain filler, I believe.) It was, for some reason, her habit to stain wood without any further finish and that made for an easier job - at least one that required less finesse and skill. So, besides self-indulgently remembering a couple of stories, my point is that it's tedious and annoying to strip paint but it doesn't require that much skill and it can easily be diy.

In a real craftsman bungalow I'd start replacing all of the miscellaneous woodwork with appropriate quartersawn white oak. Yes it will be a big project, but you'll end up with something wonderful. Stripping oak is a PITA unless it was finished with shellac or similar first because the paint gets into the grain and you end up spending a long time with a wire brush and solvent getting it out. If the trim is just made up of flat boards it might be easier to just replace, or take them down, strip as much paint as you can and then run them through a drum sander. (you can take the opportunity to insulate around the windows when you have the trim off) Our new house/addition is in an English Arts and Crafts inspired style. I incorporated a fairly elaborate curse on anyone who paints the cherry woodwork I installed.

I like your home. I also agree with you that the current color looks like an unfinished stucco job. Consider a paint color similar to the one below, it works with brick too: You probably need to sample colors to get to one that works with your home and brick. Also, if you remove the plastic inserts from the garage windows you will instantly update your garage door. Those half circles don't seem to relate to anything on your house, but the rectangular windows you get from removing those inserts would work well with your design.

Hi! Here is an article with some ideas, not sure you have seen this one yet but posting it just in case: https://www.kylieminteriors.ca/the-best-paint-colours-to-go-with-oak-wood/