Would you stick with the briarwood for the entire outside (stucco and siding) or pick two complementary colors? Yes. Don't do two colors. It would chop up the aesthetic. One color will have more curb appeal impact. btw I am loving the SW alpaca color SW7702. Do alpaca and briarwood complement each other? Technically, yes. You'd have to test carefully and check the pair under different lighting conditions because Alpaca could shift purplish.

sage greens work well, the shutters could go, or be replaced a bit larger. the front door needs to be a pop since its set back, maybe a blue tone. soft yellow trim is nice with this combo

We used Everlast wood grain siding when we redid our old Colonial. We have several farm buildings and associated maintenance and didn’t want house painting added to the list. Most people think it is wood. Our restoration contractor was initially horrified when we suggested it, but once it was done he thought it looked great and said if he had known how good it looks he would have used it to redo his farmhouse.

Because based on my research (reading and talking to Shweri Williams rep) paint tends to outlast staining? Maybe. Under ideal circumstances. But. Existing structure. No way to properly back prime the siding. No way to prime the cut ends of the siding. Stained siding breathes so any moisture that might migrate from the interior will evaporate vs getting trapped behind paint (leading to peeling paint). And your roof has next to zero overhang to help shield the walls from the elements. So, realistically, less than ideal circumstances for optimum paint performance. Before considering other variables like weather conditions during the job, painter experience & skill... No mention of the labor & material cost. To paint now, it is a minimum three coat job. Primer & 2 coats of paint. To repaint later will involve scraping, sanding, priming & paint. To stain now & restain later will require less material & a lot less labor cost. Agree with Cat and Roarah--I would go with a semi-transparent oil-based exterior stain.