I feel that if you paint the trim around the window, then you should paint all other trim. It would look odd otherwise and honestly, it would look like only parts of the home have been freshened up. There's a house I drive past that apparently buys a run of siding as the owners' budget allows. So it's been a slowly disappearing face of Tyvek wrap for the past 4 years. Personally. I wish they had just saved up over the years and done it all at once. So I also vote for just waiting until you can do it all at once. If I can barely tolerate/ignore the exterior of my house for 12 years, anyone can. I don't think the other responder was suggesting that you paint the garage door the same CURRENT color, but instead, once you do paint the stucco, make the garage the same color. I personally think cream colored house, or gray, with black trim would look sharp. Can you find more of those eaves and add them to the entrance at some point? Have no clue if it's possible, just a thought. Please make sure whatever siding you paint, you paint it all, not just what faces the street. Trim those shrubs too. Just saw that brick on the front, if that's the only place you have the brick, I'd budget for removing it. Looks ridiculous. Keep us posted.

Yes. I think gray would look good on the siding with white trim. It needs to be a gray that goes with the roof. Cute house and I love your garden.

What do you want from the house? I happen to LOVE MCM but that is not what you have now. The shutters need to go so do those planter/ bench thing on the front and for sure the shakes. But before that you need to tell us what the look is you want. If cottage is the plan then let me know. Landscaping is a huge part of MCM or cottage . A bit more info please. BTW I am thrilled you do not want to paint the brick.This is what I would aim for but I need your info.

Wow! I've never reached out to this community before. The response has been wonderful! Thank you so much for your work and ideas. An especially big thank you to Flo and Melissa for the visuals. I really appreciate your time. You have given me such great ideas and much to think about. Thank you, thank you!