I like the idea of black windows. I think a medium gray siding color would look great with the brick and the black windows. This doesn't look like your house, but I like the black window trim, red brick and medium gray siding color... You like?

Executive Calgary Semi-detached · More Info

yes, yes and yes.

Are you also redoing the trim, soffits, and gutters/downspouts at some point soon-ish? Since those are brown, I fear black windows and doors will look out of place. Temporarily that's no problem, but I do think you should have a plan for those.

You have some out of place elements on your home; the front door style and the gingerbread up top. Remove/replace those and you'll have a classic. Keep window and trim color consistent.

You have a really cute house and it will be even better when you're finished with it! I like your inspiration pic above a lot. Very achievable with where you're starting and a great update for the house :) Just pleeeease keep the brick?

Just curious, can the siding can't be removed if there is brick under it?