Looks like you have it thought out. I would suggest picking your roof color before you pick your paint color. Paint color is much easier to change over the years. Personally, I would pick a very neutral shade such as grey or black (like you suggested). This way you have many other color options for the color of your home as time goes on. You can find a beige/grey to soften the red in your brick. Versus a cooler grey (Wow that looks really blue next to the top one- but when by themselves, they both look more grey) It will be nice to see how your roof impacts the look of your home over the course of the year and throughout the different seasons. I am not sure where you are located but a north facing home, in the northern US, a grey will take on more of those blue tones. Yes, I would make those attic vents blend in. I am not sure that I helped any. Good Luck!

I really appreciate these suggestions and visuals - thank you! I will take pictures from some additional angles; the house is very boxy, and is currently one color of stucco all around, with one trim color (dark brown), with virtually no relief or break-up of that vast expanse of off-white stucco. I have been thinking about making the front porch body a shade or two lighter (or darker) than the body of the house to add a dimension/ depth; adding shutters to the 2nd floor windows is something I hadn't considered but helps add interest - thanks houssaon for that idea! Oh - there are no flower boxes on the 2nd floor - just on the outside of the enclosed front porch (which is basically the whole 1st floor you can see from this picture). OK, more to come soon - thank you for these suggestions!

if the roofline is going to be that prominent like the 2nd pic, you may want to go w/a slightly lighter roof tile. maybe a silvery gray instead of a charcoal. I did mine w/charcoal spanish cement tile roof, wrought iron trim, swiss coffee body and wood look garage doors. my home is a mediterrean style it used to be golds/brown, beige. hated it. when this color gets old, I'll repaint. not a big deal

Thank you for the compliment. It is BM Grant Beige, a more medium tone beige. I really do like the color a lot. But, I’d like to try more off an off white for this go around.