We currently have brick and aluminum siding on our colonial home. We are looking into residing the aluminum (primarily for aesthetic reasons due to denting and fading and 25 years of wear and tear). Considering Hardi Plank or foam-backed vinyl to replace aluminum. Need some advice:

1. Any suggestions or advice on those products? We would be going with a 7" reveal in each case. The cost difference isn't a major factor. We are leaning towards Hardi, since it we like the look, but are concerned with potential maintenance and gaps where boards butt and meet windows/doors with this product (we live in a country setting and bugs/bees/woodpeckers are a consideration as well as our North East US weather).
2. We will also be replacing the dentil molding- should we go with smooth, slight pattern or dentil?
3. We will eventually be replacing the windows, but would prefer to wait a couple years (to smooth out the expense)- would it be significantly better to replace at the same time?
4. Current contractor estimate includes leaving existing window trim. Everything else will be new (roof 2y, new siding, gutters, facia, etc.), would this make old window trim stand out? I wonder if wider trim around windows would be better? Replace now or when we replace windows?
5. For colors- Cobblestone (seems to be close to existing color and brick grout) vs Monterey Taupe (a bit deeper of a color)?
6. The contractor plans to use Azek trim on the sides. Wondering if we should go with white (match trim) or paint to match siding?

Any thoughts/advice is appreciated!

Picture of our existing home