It's been over 60 days and I still have not primed or painted the new stucco. We have had a lot of rain so the stucco guy is on my back again to at least prime the new stucco areas because they may start cracking or holding water in between the old & new coats of stucco. FWIW, We're starting to enter the most hot & humid time of the year and the height of in hurricane season, which has shifted my focus to retro-fitting new hurricane impact doors & windows. That said... How long can I leave new stucco bare without risking harm to my home? If I prime these new stucco areas now, am I just going to have re-pressure wash (and re-prime?) these areas in Autumn when I paint the entire house? Thanks

Sure, why not.

Good choice in brand, not so much in sheen. Personally I would never use flat on an exterior, flat is a good dirt catcher.

I actually don't mind painting brick, though I strongly prefer staining brick but so long as you use the correct product I actually like the look of painted brick. You must use a vapor permeable paint, and painting increases the maintenance required for brick considerably, but if the look is completely outdated or inappropriate to begin with then sometimes painting brick can really update the look. Having said that I live in the land of red brick houses and they bricked everything even craftsman influenced houses where brick is not appropriate at all. However, I think painting the brick is the least of your problems. If I owned your home I would start by planting a nice tall cypress (or anything tall and thin) along the left edge that distract from that wide brick border on that side. I would then cover up the lower brick border with some sort of hedge or bushes that break up that line between the brick and the siding. If I had the budget for it, I would remove the vinyl siding and either go with a darker grey (or a blending color) wide board hardie type siding or staining the brick into something softer. Before you take my advice, this isn't something that I excel at personally so other posters might be giving you better advice than I am. The other and probably best option is to remove some of the brick, add brick in other areas and then paint or stain the whole thing to update the look, however, that is a significant expense to accomplish what a great landscaper can do for 1/5th of the price.