The white trim needs to be close to the color of the windows so they look more cohesive instead of two separate elements pinned together. Also the trim around the door needs to be the same color as the door for the same reason.

hi im a third generation stucco plasterer from north west canada. i dont have alot of time to give you advice but when i came across you problem i felt compeled to respond. so here you go , any loose stucco should be chipped away leaving the paper and wire on to tie into when you add more wire. do not attempt to put another 3 coats over the exsisting stucco. add the base coats twice if nessasary 3 times to make a level surface making the whole wall flat. let it cure. the longer the better, even a year would be ok. very important part of stucco contractors skip is flood the wall after application before it cures and repeat often cement will cure harder under water.. then skim it all again with base and apply finish as usually done on a new job. you may need to strip off paint depending on weather its 10 coats, if it is then striping may be to difficult. if the paint is flaking off then yea wash. if it seems to have good bond perhaps if you hit it with a rotery wire brush you wouldnt need to get it all off because you will wash it then use welbond. this is a glue that is mixed with water and rolled on and or added straight to the mix .look for me on facebook @ armor exteriors and stucco solutions . i hope that was helpful

I'm glad you're firm about not painting the brick. The brick is a natural, textured feature of your house that allows it to breathe and requires litte maintenance over time. Since you have a visible light brown roof, your trim needs to work with that as well as the brick. Here are houses with the same varieted brick as yours, one with a brown roof. You can pick up a greige for the trim with maybe a light blue or yellow door or this light green. Just don't do white--too much contrast. I'm showing this for the tan. Though the door is handsome and like yours, a lighter door might be better on your house since it's receded and looks too dark right now.

PPF., thank you for the suggestions. It does look better with the garage down like that, but we will need to keep it higher for the bonus room. Maybe I could just get rid of that bit of roof altogether, push out the window section, and that would all become one wall? I will mock it up later when I have a minute. As much as we love board & batten, I do think going all stucco might be the best choice. It does need to be cohesive. And that ties in with what Mark was saying. Even though we don't have unlimited funds, I don't want the exterior screaming "we cut corners!" I really appreciate all your input!