1) What is the longest ride you've ever been on? 101 mi
2) What is your longest distance in a training (something repeated weekly or monthly) ride? Generally ride between 17 and 20 miles/day. Usually one day get up to about 25-30 mi though
3) What do you consider your "this is starting to hurt" mileage? Depends on climbing, flat I'd say 75-80 mi, Really hilly though and it would be much sooner.
4) Do you have a distance goal? If so then what? Shooting for 5000 miles/yr. Currently around 2600 for this year. With a mild fall and early winter and I think I have a chance, if the weather turns ugly in October I probably won't.