A few factors to consider here. Weight will play a major role in distance, as well the number of small hills and steep hills.
Do you care how much you slow down on steep hills? Most boards that are geared to 20 mph will slow down to 10 mph or maybe even less on steeper hills. It depends on torque.
My build for that price would be…
carvon dual v2.5 (~$400)
dual vescs (~$360 with warranty)
And a massive 12s6p18650 battery (48 cells @ $5 = $240, if @ $8, $384)
Power switch (~$35 if you get from JDogAwesome)
And whatever board you want and an enclosure (many different people make them and since it’s not a mving part, I don’t think theres too much of a difference that you will any effect on your board. These should be together $200 or less.
So that’s $1235 - $1379 for an entire board that will get you faster than 20 mph and more than 20 miles of range. The 12s6p is a must IMO if you want the range.
Also, a charger and bms would be another $100-$200, which is a must. Others can tell you what ones are good.
I am 6’2" and weigh 150lbs most likely it would be one big hill and the a super huge downhill I would like to be able to break and reverse on a hill regen would be nice too.
Vescs are highly recommend. They are the best speed controller and they have regen. The only speed controller btw that was made specifically of electric skateboards.
Since your not afraid to spend money, you have the luxury of getting some really nice parts in that price range.
I think you want a bigger battery than the range you need cause sag will be some slight amount, and its better to not full charge and discharge. And if you have the money, go for it…