At 6'6" and a very skinny 220 pounds, it has taken 40+ years of expiriments to get a bike that does not cause pain. I switched to recumbents for 5 years or so, but missed the road bike. But finally I got everything super dialed in so that I feel equal discomfort at all my touch points, but seldom pain.

My essential engredients included a pro fit, steel frame, 42mm tires, rando handlebars at a moderate height, double layer of cork tape, ISM saddle and unpadded gloves.

I can go 3 hours non stop, but if going longer will stop every 2 hours. I am constantly moving my hands and butt, and stand every 10 minutes or so. If I ride slow, the extra pressure on my hands sometimes leads to electric shocks running up my arms, but no numbness. Other than commutes, I seldom do rides under 50 miles, but rarely over 6 hours. After that, it just isn't fun, regardless of my desire to do rando.