I really like the "pay $30 and get a t-shirt or bottle, SAG support, traffic control at major intersections, rest stops with refills and yum-yums, and a kick-butt lunch" rides.
I wouldn't mind doing the multi-day, shake some trees until you find $250 rides, but they are always a plan well in advance thing. My military career has never made long-term planning like that very feasible.