Thank you! So much great feedback. Sadly, the paint job is a necessity rather than just aesthetics -- paint on the back side is failing pretty badly & peeling off in layers. (After reading up on the paint forum, I think it was just too many layers of latex on top of old oil paint without adequate prep.) Maybe we will keep it close to current color. I'm not sure what color it is, but I'll have to stop by the BM store and pick up a tab for Briarwood. I think those color visualizers are just a bit off, at least on our monitor -- Down Pour is a very smurf-y blue on my screen. Luckily, SW store is right down the street. Of the SW colors, we liked Mineral Deposit -- gray, but not quite so dark. Johnmari, my wife said exactly that about warm trim looking bad with cool gray field color. I just want to get away from the current ultrawhite, just tone down a bit but not too much. Shutters? I think we will someday, after we've finished the essentials. Of course, being picky, I don't want to just screw aluminum shutters that don't match window size on there, so might be a while given that real shutters & hardware are pricey. The suggestion about doing the sash black is good--that could look really sharp and make the windows pop a bit more until we can dress it up a bit more with shutters. Absolutely agreed on the landscaping solutions. Could be more varied and it would add a lot. THANK YOU for all your suggestions, such a helpful group & nice little corner of the internet.

Before and after. We are very happy with the results! In addition to the paint, we did a new door, said so long board and batten around the base and the corbels that were falling off, and bye bye to the decking. We also poured a larger porch area and added a brick patio to the front. Still need to get up on the ladder and get the last bit of blue tape off the window, but I was too excited not to post! One more coat coming to the shingles, too . We painted most of the house ourselves, hiring out only the tallest parts. Thanks to all for the advice and encouragement!

@Beverly @WestCoast Hopeful Oh my goodness, I love this porch idea SO much. It takes the porch and yard from two separate spaces to one big, friendly space. Our builder will 100% NOT do this for us, so we'd have to do it afterwards on our dime, but I love this transformative idea! We probably wouldn't lay concrete across the whole back, but maybe a smaller area with a gazebo or something. I stopped by the house this afternoon and walked around at ground level behind the house. (I haven't done this too much because we've had a lot of rain the last few months and it's super muddy.) When I was down there, I learned a few interesting things: First, the area that I thought was most usable -- directly below the porch -- is actually not the most usable. It has more of a slope than I thought. You can see it better here: It's still going to be useful, but the largest level part of the yard is in the corner where I was standing when I took this photo. Conveniently, this is also the area where the level part goes deepest towards the back of the lot, so it gives us the biggest usable level space. This slope right below the porch means that the big wide centered steps that @Beverly suggested would have to go out significantly further to actually reach the ground. It would probably consume most of the usable space below the porch. But that's more acceptable now that I know that the corner is the prime real estate in the yard. Here's another photo that might show the slope better: The other thing I learned is that the left side of the porch is actually not as high as it looked from above. Standing on the ground, the porch is slightly above my eye level, or about 5.5' up. And since the land keeps rising to the left, stairs going along the house would only have to cover about 5' vertically. We looked at the other stairs from our same builder and estimated that they're about 40 degrees from the horizontal. So one trig calculator later, and it looks like the stairs probably won't even come to the guest room window! So I think we'll go with the left stairs for now and then look into a set of fancy wide porch steps down the line. Thanks, everybody, for all your thoughts and suggestions! I'm really happy with the left stairs for now and the awesome stairs later.

Agree that removing the screens would make the covered area more inviting when viewed from the pool and would enhance the connection between the covered space and the pool area--if you're sure that bugs won't be an issue. (There will probably be less breeze under the roof than out in the open.) As a compromise, is there any way to make the center bay fully openable (and also closable if needed) and leave the screening in the bays on either side? As for fire, the least expensive option is a freestanding fire bowl/table surrounded by chairs, most logically in the far corner near the tall palm, it seems to me. (Do I see a fire bowl there already?) A permanent fireplace could also be built in the space between the paving and the back fence, I suppose, centered on the left-side paved area for furniture arrangement on both sides. A more expensive option would be a double-sided gas fireplace set next to the spa, so it can be enjoyed from the spa itself or from a seating area behind the spa, overlooking the pond and woods. I can't tell whether extending the paving there would make a large enough seating area, or whether the retaining wall would have to be moved farther out as well.