Home exterior - order of operations

[candreco]

I'm currently at 1 on my house (dumb shutters, front door style I REALLY dislike, siding that's fine but will need to be replaced eventually regardless). Planning to wait a couple years and then just do everything at once, though I'll probably repaint the existing front door in the near future just to freshen it up. I am at least working with black shutters instead of a harder to coordinate with color.

Neighbors down the street just redid their exterior with no shutters, chunkier trim, and some accent siding around the front door. It's gorgeous and I'm so jealous, lol.

[origami]

Another vote for change the door, paint the shutters a dark/neutral and skip the siding for now. My shutters are black and my front door is olive green (prev homeowners picked it). Looks good IMO but I actually prefer the inspo pic you shared that is stained wood instead of paint.

I'm probably in the minority on this, but I think the lack of shutters on your neighbor's house makes their windows look too small. Also not a fan of the brick front/siding elsewhere. I used to have that on a previous home and someone called it a mullet house. Still not over it lol.

[SusanBAnthony]

My parents house is nearly identical to yours, including the siding, shutters and the maroon!

They took the shutters off, meant to repaint them, and ended up just filling the screw holes instead. So I'd say take a few off and see what it looks like.

I do think colonials look naked without shutters. If you are going to go with thick trim I'd try to do something else to make it look less colonial like adding a front porch.