Hey Roguedog...
I rode the Cindy for the first time last year. I'm not a very strong rider (more of a plodder and I suck on hills) and I thought the course was pretty easy. There is a hill in a residential area at the beginning of the ride that was a little hard, but not too bad and then Cross Road (which I think Trek was alluding to) that wasn't too hard either. Just keep turning the cranks. I didn't do Lemon Drop because of the aforementioned head winds. I quit after the lunch stop and took the paddy wagon, er, I mean the SAG vehicle back to the start. I'm still glad I did the ride, though. It was fun! You'll be fine!!