This year is my 3rd time riding, 5th time participating (crewed one year, led or I should say swept training rides another). Yes, it is an impossible goal and I've done it twice.

I gotta go to work right now so I'll just vote:

Encourage him but this should be a long term goal.

Can he train, fundraise if he wants to but crew this year and ride next?

His goal should be to do at least one or more centuries this year, maybe even one of the other AIDS rides, MS 150 etc. Come crew with us, it's much harder than riding anyway and do the long ride NEXT year.