Try different shoes.
I for example get foot fatigue after like 4km on my pneumatics if i wear shoes with a soft sole. Hard sole = no problem. On my street board i can wear whatever i want
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You can also stretch & exercise your feet 1 at a time while riding 
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I disagree with this. Since esk8s are self propelled, there’s a much greater focus on your rear leg to brace against acceleration and braking, compared to DH where you just need to keep your balance on the front trucks and the rear trucks follow. If boards were FWD it might work better, but with the standard setup a DH tuck feels sketchy anywhere past a mild acceleration.
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Are your trails paved or dirt.
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Paved or dirt trails?
Thanks for typing out what I was thinking
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You could also put traction pads on your deck to eat up some vibrations.
Only thing you can do with that setup is foam grip tape and better shoes/insoles.
Everyone has probably had numb feet at some point. When I first started esk8ing my leg goes numb after about 3 miles, but it had a lot to do with my obsession with carbon fiber decks. Even with that, over time I was able to ride longer and longer before my leg gets numb, I would go on 25-30 miles right easily without issues.
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From my perspective riding shit roads on thane boards shoes make a huge difference. I also use “skate shred” inserts in my go to pair of Globe high tops. You are already using some of the most comfy street wheels on the market. If position and footwear cannot get you where you want to be I agree that pneumatic tires are your next best option.
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Paved trails.
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A teaspoon of cement sprinkled on your weet bix every morning for a week will do wonders.
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Good shoes do wonders for comfort. If you have a few different styles of shoe, take a ride in then all and see what I mean. Different sole angles and features can impact your ride a lot and everyone’s foot is built a bit differently. Padded or gel insoles also do wonders,
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In industry in the UK we have something called HAVS (hand arm vibration something or other) it’s a regulation designed to prevent damage to the small blood vessels in the hand causing ‘vibration white finger’
I wonder if this is going to become an issue with esk8ers but in our feet?
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this works for me very well. buy a sheet of adhesive foam, and stick a sheet of grip tape out of it and go from there.
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Its an absolute motherfucker to remove
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oh yeah, heat gun helps dramatically though
I doubt it. He’s probably just new to it and his feet will adapt. I’m 52 and esk8 barefoot. No numb feeling. Better proprioception.
My man 
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Anatomy has something to do with it as well. I have high arches and if I don’t use inserts with arch support, I hurt after 20 miles. Same on the bike and snowboard.
Brave man, I won’t try it since I tore most of the sole from my feet trying to analog sk8 barefoot. I still get flashbacks of all the blood.