Didnt read the whole thread so some one else may have said this already. If you can carry a cell phone with you incase you cant finish it and need to call for a ride back.Other than that i say go for it. Nothing wrong with pushing your self to your limits and calling for a ride back when you hit that limit and cant go on. If you feel winded after a larger than normal hill climb shift down take it easy. Try to keep the other riders in your sight range once they reach the limit that you can see them start picking up speed again. Youll catch back up and likly finish the ride with no problem. If your in a area like i am they will probably take routes where theres a rider hang out or 2 and stop there. Probably some custard stand something like that. Of the 4 bike clubs in my general area 3 plan their routes to hit the same custard stand down on cherry street.