Difficult to paint and costly if done correctly. If you have white toned walls there is ZERO room for error when doing black trim. Every single line shows and must be dead on. Its like black caulk on a white tile. It also doesn't cover like you think it would especially with a semi gloss so more coats and sanding between coats. If you choose a black tomes paint go with an eggshell sheen as it doesn't show defects as much. I would save it for a feature such as a bookcase and then paint rest of trim exact color as walls only in a higher sheen. It gives a clean modern look. We do this all the time and everyone swears the molding are a different color than the walls as the sheen alters the color perception.

@Jan Moyer and @houssaon I agree. I had been looking at these dilemmas because my front door is not at the front, ha, ha. The bottom line from all the recommendations has been to emphasize the front door, not the garage doors. So I would say: paint the trim AND garage doors the same as the house. For the same reason the house numbers should be located by the front door, not over the garage door (answering your second post). Good luck with your project!

decoenthusiaste: Thanks for solid advice. The seller replaced the windows in the last couple of years - they are a beige vinyl. Good for energy efficiency, but don't love the color. But if we're sticking with the current brick colors (which are not my first, second or third choice on color either), then they blend. The picture with the hedge is somewhat dated from the realtor listing: the snowpaclypse of 2021 killed virtually all the hedges, and the foundation work took care of the rest. I have a landscaping plan: just need to finish the under-foundation plumbing repairs before we can start. The trees prevent grass from being a great option - so we'll probably do a large bed with hostas, ferns and other shrubs. 100% agree about the tacky edging bricks. My son works in construction, so he'll be most of the improvements (and yard work). The front door is currently forest green - would you paint the door the same color as the trim? Also- are you saying that the windows are not type to work with shutters because they butt up to the eave of the house?

I have the same wood trim - I think. My crown moulding is about 2-3”. I hate the dark thin lines. I plan to beef up the trim, and baseboards, and paint them white. However if you love the wood crown, you could consider adding more wood under it to make the lines thicker, and see if you want to stain it. If you paint, you could add a lesser quality wood and caulk any gaps. You can treat crown/baseboards differently than window trim which can be different than door casings. In my house, all those lines are thin, so I will be beefing them up and painting them. However I will be stripping and restaining the wood doors, so there will be a lot of wood accents in the home without the trim needing to be wood. Think about what you would like to do to each type of trim, and start with the one you dislike the most. Because of those door panes, you might consider adding to all the door casings and keeping those wood. If the windows are really nice, that wood could stay as well if it is chunky enough. The baseboards seem to blend with the floor, so those could be painted or replaced with something bigger. I like the arch. It might help to repeat the shape somewhere. Maybe a mirror or something. I like your arched front door too.