Salty, I face the same issues you do.
It seems there are some things worthwhile.
The Rohloff will a long time essentially maintainence free. It also means you can use a chain for a long time with no problems (or so I'm told.)
Will an eight-speed do? Sure! If you move to Cleveland or some other flat place. If your lowest gear is low enough to comfortably deal with 18th street, the high gear would slow you down on any downward sloping route.
The 11 speed would be marginal.
Or course, if you had the right 8 speeds, an eight speed would be great, but existing hubs are not only a narrow range, they have the order reversed from what is useful - the high gears are close together, but the low gears are far apart. That means the places where you want more gears, you won't have them.
An 8-speed with a triple chain ring might work OK, but then you would still need to change your chain. And the far-spaced low gears would still be an issue.
I don't know about internally geared cranks, but a 500% range is about what you would want, for sure.
The gear range, the disc brakes and teh heel clearance all strike me as valid issue.
We live in the USA. People spend $5000 on a bike just so they canh go go .05 seconds faster than some other recreational biker. That cash is mainly adam's apple measuring anyhow.
Your bike would not be.
It's possible you could get what you want, with the disc brakes and the Rholoff, for a lot less than $5000. (I might be wrong.)
But, yeah, you would have to spend $3K and that is some cash.
Think of it this way - the difference in performance between a bland, practicle car is nill - your speed is still imited by the law, not the technology, you have all the comforts in teh cheaper car.
But people still buy SUVs instead of minivans, they buy "sporty" (HAHAHAHA!) cars, luxury cars and flashy cars, instead of practical transportation.
The only reason I see for this is that people watch TV ("I'm too clever to let the ads affect me!")
The difference in price between a decent car and the car the thieving marketers want you is almost all profit for the cart companies (and advertising expenses). The difference between a decent car and the flashy trash you most often see? That difference is a lot more than you are thinking of spending on a bike.