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jakemcree
Forgetting the distance it's easier than TCR. No languages or money issues, fairly easy to resupply and it's a fixed route so surprises are reduced since you get more info every time the race is run. Weather can be a factor - it's damn cold in the mountains at the start, can be hella windy in the middle and then steamy bastard heat towards the end.
I've still not done a clean run at it - both times I've fucked myself up with some stupid issues at the start - first year was the calf guards rubbing a tendon raw (like I did with armwarmers in RATN) and second year I'd somehow managed to setup my seat totally wrong height and fucked my knees to the point where I was looking at quit options.
People on the route and interested tended to be amazingly nice although there's always the odd loony. Roads are good quality but there's some dodgy driving and some big trucks you're sharing the road with sometimes.
Big, easy hills at the start and then it gets rolling in Missouri and harder climbs in Kentucky. Everyone underestimates the climbing at the end because the 3000m Hoosier offsets the gradient profile.