Sure, why not.

I suspect the trim is original to the house - why not just paint it a more harmonious historic color, what am I missing? Sorry to be blunt, but removing historic trim and replacing it with.... what? .... because you dont like the color is.... well, lets say pretty extreme, not to mention far more costly than a few gallons of paint. A good starting point is to try to find the first layer not that it has to be that color again, but it will inform you re: what the original design intention was - also google images of the period - even though its kinda Dutch colonial it will have had the influences of Arts & Crafts, Art Nouveau etc. I would eliminate the stark white and gray entirely from your exterior palette .... I know thats kinda radical to the Houzzzzzzzz folks, but those just arent the most flattering choices for red brick. What is the black shingle - is that wood shake or asphalt or what? There again it would be good to suss out the original intention of your house's design. Was it meant to match or be the same shingle as whats on the roof? Ive occasionally seen houses with that type of exterior - with shingles on the vertical second story walls - its a kinda cool look and you wouldnt have to paint up on second floor ever. The more you can remain true to the original intention the more everything will fit together and make sense and be pleasing to the eye, Replacing house parts and architectural features like trim with modern replacements starts to look too hodge podge - not good.

Thank you, everyone, for your comments! I guess we should remove the porch railing! Most of the aluminum storm windows are missing panes so I was planning to replace them with white vinyl when we paint. The windows are an uncommon size, though, so I'm a little worried about the cost. There are only a few original windows, but the "new" ones are from the 70s, so they're all old. All the windows are wood and painted white-- and they're ALL drafty and in need of re-glazing, which is why we need the storm windows! I'm adding a better photo of the front porch-- and the chickens. The color I picked for the front door is close to the color of the sky. sheepla-- is there also no hand rail on the steps of your porch? I'd love to see a photo!

Thanks for feedback. Can't change the roof color for another decade I suppose until it needs replacement. At that point seems like the roof's wings could be removed! Garage door is on order (this is photoshopped but same colors). Light Grey / silver would probably have been better but lesson learnt as it seems too late now - would have to pay a whole extra day to repaint the section they already did.