Looks great! Thanks for the pics. You should really come by my house to see our grading/fencing. I think it may give you some ideas or context to see a similar slope on the downhill side of a pool in person. Putting the fence where the new grade meets the old grade makes the fence disappear when viewed from the deck area - really cool effect. You can certainly do a retaining wall on the lower side but it is absolutely not required for your lot setup.
Don't buy into the "regular" vacuum. It's like apples and 8-tracks. I never want to leave my cleaner (of any type) in my pool because it makes it look unfinished - like you forgot to put something away - it kills the aesthetics of a beautiful pool in my opinion). That said, the real reason is because of the quality of cleaning and then brushing the surface is a solid bonus. I hope you get other similar feedback because I feel strongly about robots vs. pressure/vac. cleaners. Getting a linear main drain also eliminates ANY possibility that a robot would get hung up on the drain.
PM me if you want to come by.
All of your Cons are Pros! Bigger pool, deeper pool, automation, higher (well a trade-off - see above), fewer trees nearby, no sprinkler to maintain (grass goes dormant and comes back saving water in the meantime - outside of M/H C's. no one has sprinklers in central MD

) Ok, more money spent is a Con.
Great news on no rock too!!! So exciting!