Well...personally at this point I would be staying away from anything that came from a certain island. After 8 years of even the best kept storage conditions, some of mine I picked up in Canada are starting to actually lose some flavor (2003 box code, I bought it in Dec 2004).
I'm somewhat anal, so I would probably write out the next 50 years and then pick two smokes a year for each year, regardless of the cost, then I'd splurge and buy all of those smokes and rent a locker at a local B&M or buy a special humidor and keep then tucked away with the list for that special day every year
