I don't know, I think the Partagas Lusi's will hold up to 50 years better than the HDM's will.
Then again, could get a cab of RASS, I know they age well with limited time, not sure how they will do over that amount of time.
I feel for you, ben, this ranks up there as one of the coolest ideas concerning cigars I've heard, but it's also not going to be easy. I'm going to buy a box of cigars when my child is born, and smoke one every birthday, but that's only 20+ years, and only a box.
The reason I brought up bolivar is because I feel they have the most aging potential, but if you don't like them, it's a moot point.