Impossible to answer, methinks. The Cuban Monte #2 sure isn't a bad answer, though.

The single best cigar I've ever had was actually a Davidoff Millenium Series Churchill. Had it on the day I got engaged. But I think the reason it was so damn good was that it had sat in my humidor for several years (at $20+ a stick, I decided to save them for something a little more special than a beer in the back yard).

I wouldn't mind a lifetime supply of those. Then again, I almost never smoke the same thing twice in a row .... so your hypothetical would be torture