Giro Di San Diego...

The Giro Di San Diego, is it too much?  It is not enough?  They seem to offer a long of levels of "Fondo" fun.  I'm not sure I'm ready for the Gran Fondo, I know I could handle the Piccolo Fondo easily, but maybe the Medio Fondo would be a stretch a small stretch.  So should I attempt to blow my legs out on 100 mile ride or just push myself slightly for a 62 mile ride?  Either way I think I'm going to want a few more granny gears. What the over/under on the number of flat tires that I'll get?