Stephen,
My favorite cloth diaper is the flat prefold gauze diaper from ACD(Adult Cloth diaper). I wear a medium and have a 36" waist. I'm also 6'-3". You probably need a large. I adjust my needs with this diaper with cloth baby diapers. As I wear these at night, I'll usually add two or three with the adult size gauze. For day time use, these work well too, but my be a little bulky at the office. I think they would do OK while hiking too. As long as the diaper is not too small, mine stay on with no problem pinned.
As far as pooling at the bottom of your plastic pants, the majic of wicking will prevent that. Now if you have a huge flood all at once, you may get some pooling. Over time, the cloth diaper wicks the urine untill most of the diaper is wet. You'll have some trial and error, but I really love cloth diapers. The primer on this site shows a way to pin on a diaper, but I can get by with just two pins. Any other questions, just ask! .....Paul Martin
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