Ass complications: Bag Balm. Or A+D ointment. And make certain to clean at least that certain area at least once a day.

I can remember an age where I rode 108 miles so that I could barely walk that evening, but I was still able to get up and go for another hundred the next day. My main concerns would be whether you can tell between getting tired and getting hurt, whether you have a plan B in case you start getting hurt, and whether you're actually going to enjoy yourself biking that long each day. Biking to your limit can be an exhilarating experience, but it gets old after a couple of days. Planning for 65 miles a day is much more doable for somebody who is in general good physical shape.