I lived with cedar for many years and understand how you feel. I suggest you consider HardiePlank or HardieShingle Siding. It's a cement fiber product which is nearly indestructible; it doesn't suffer from things like cracking, rotting, hail damage, or termites; it comes in various colors; and has a 30-50 year warranty depending on the product. I have no connection with the company other than the fact that I've had one of these products on my house for quite a few years and it still looks like day one. Here is a link that might be useful: James Hardie siding

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.

I don't know where you live, but have you checked Weather Shield Windows. They have aluminum-clad wood windows that would look great on your home. Bronze windows would be great on your home https://www.weathershield.com/Product-List/Weather-Shield-Contemporary-Collection They are a national brand and you can get competitive pricing. Replacement windows are typically a huge rip off to the consumer. , I'm not sure I would consider vinyl windows for your home. Thicker frames, less glass typically on vinyl. I have personally never heard of Simonton Vinyl Windows. Have you bothered to check Andersen or Jen Weld from your local big box store?

I really love the look of that SW Anonymous color next to your brick. Do you think you think you might want to paint your garage door the same as the siding? I also love the Cajun Red as an accent color, but don’t see where you could use it, except maybe in your landscape plantings, or Terra Cotta pots.