Regarding the VSP, while the landscape firm is not technically wrong, for the relatively low cost to get one over a 2 speed, PBs really shouldn't be installing them now anyway. Come July 2021, main pumps for filtration will be required to be VSP, why not just make the switch now?
Could do a robot but more complicated device, have to have a power cord connected vs. just hooking into the side of the pool. Didn't seem to be philosophy issue, just trying to keep things as 'simple' as possible.
Really, if you want to keep it simple, removing the built in cleaner and using a robot is as simple as it gets. Plug in, drop in, watch it clean. Maybe the robot itself is a more complicated device than say the pump used to power the installed cleaner, but it actually removes complication from your whole build, to remove the pump and plumbing for the built in cleaning system. Also, if the issue is "we need to have power nearby", you are already going to need power nearby for the pump you will need for the auto cover. As bmoreswim mentioned, you put the pump on top of the cover when you close the cover, and plug it in, so you will need power somewhere.
5. He's asking about the Automation - although given the rest of the discussion doesn't seem like we have a lot to automate.
Regarding automation, it sounds as if there isn't anyone on the build team that is familiar with this, so it may be less of a headache at first to skip it. Someone will need to hook it all up, and program it, and if they are comfortable with just timers, and that works for them and you, not sure I have anything to say that would change the situation. Just know, there are things there to automate, they probably just doing normally automate them.
Don’t get me wrong, your pool will be wet and wonderful, just so many things that can be tweaked. Everyone has to allocate resources and make choices. No wrong choices, except maybe that vacuum.
Well, I would also say the following statement is wrong...
6. He thought two lights was plenty, doing more would be overkill.
Three lights are not "overkill" for a 15x30 pool. Take a look at my construction page, you can see three Microbrites in a 14x30 pool, and they seem just right. Two may be "ok", but three would be better IMO.
Good luck with the process! I know there is a lot of information to process, and a lot of opinions. some of them from some of us may be strong, but that is usually because we went through the same discussions as you, and remember when a PB told us something we found later to be not the best solution.