1) What is the longest ride you've ever been on? 100 Miles and a decimal value
2) What is your longest distance in a training (something repeated weekly or monthly) ride? Weekly minimum of 180. No maximum.
3) What do you consider your "this is starting to hurt" mileage? Depends what I do. If I climb the 17%-23% hills that go on for about a mile (with a few short 6%-8% "breaks") then I think I'd be in pain pretty fast.
4) Do you have a distance goal? If so then what? No, but I do have a time goal.