On the skimmer, it's asking a lot of one skimmer to keep the pool properly skimmed for that amount of surface area and what looks like a moderate or higher level of potential tree debris. With a full reno planned, I would certainly increase returns to 3 or 4 (from 2) for circulation and skimmers to 2 (from 1). On the winds, certainly a lot of wind is going to be coming towards the house. But I know from how stuff blows around our house, when wind comes directly at the back of the house, it returns away from the house at ground level, which would be across the pool surface. And with your pool so close/under your house, that may be the case. But regardless, there are many lines of thinking, but my setup for that pool would be keep the existing skimmer, we'll call it bottom left looking out from the pool and I'd add the second one top left (still on the side wall). Then I'd put three returns along the right side, basically moving water right to left. I'd also include a deep water return coming out 6' deep below the diving board towards the house, for warm water circulation (benefit of this deep return is debatable but if heating a pool, it does provide some benefit and no downside). Ideally all skimmers (for sure) and all returns are individually plumbed back to the pad.
Definitely SWG.
Drains - If you are going to replace the lines anyway, absolutely go with the linear channel drains that allow you to add pebble to the covers. The are much more contemporary/modern looking and will match the house style better. Also, there is zero chance your robot will get stuck on them. Any round drain causes potential for robots to get stuck (not those with 3 brushes, but definitely those with 2 - the robots often get off by themselves after 30+ seconds, but not always).
Filter - If you have been happy with sand, and know it, keep sand. Only downsides are maybe more water use due to backwashing (not a huge amount/issue) and they are much slower to clear a green pool during the last and slowest "cloudy" phase. But if you pool stays clear, which it should, the that's a non-issue.
Heater - Full renovation...replace. Get a new Raypak to do with your Pentair or whatever automation you go with.
Pump - VS of course, anything else will be illegal soon, if not already in OR (and everywhere).
Fire pit - We have a real wood mobile fire pit that we use a handful of times in the summer, but also in the spring/fall. I love burning wood so it's a simple must for me personally. But I expect in OR, you'd want a gas fire pit if you do one. Another option for outdoor heat is to go European (like they have at all their outdoor eating areas) and install a gas heater into the ceiling of the covered overhang. Then you'd get a heated outdoor space with no space taken up and it would still be poolside.
Slide - Definitely replace. It just dates the whole area. Get a TurboTwister or similar.
Corrected CA to OR. And added slide comments.