With regard to your summation, which is very thorough;
Jandy won't sell direct to anyone that is not a distributor.
The amount of control you will get with upgrade to a newer Jandy chip/board/upgrade kit, etc. is very extensive. The amount of fiddling with speeds/run times/etc. is fun at first, but the reality is that once you find settings you like and that work for your pool, they are seldom changed. Some here run their VSP 24/7 at one speed and it works for them. My VSP is capable of 8 programs, I use three. And I only need two, but I set them 14+ years ago to try, liked what the pump did, and never bothered to change to something else. Pool is clean, SWG is happy, spa heater works when I need it to.
If you really want that control, and have a Jandy 50-pin board, the R0466801 chip will upgrade the system for between $400-$600.
Old chip unplugs, new one is attached, reprogram and you're good.
If you want Wi-Fi, you can always get an iQ30 antenna later.