A lot of good observations here. Definitely stick with aged versions of tobaccos that are in production and available. Most blenders turn out tobaccos that have been aged are are ready to go, but not all blenders do that. I've found Peter Stokkebye blends to need aging before smoking as they are released a bit "young" for my liking, and the same goes with C&D, which is partly why I cellar very little of these blenders. PS-LBF is cardboard when released, but given a minimum of 4 years turns into something amazing.
Aging doesn't necessarily improve blends, it just changes them, and whether the change is an improvement is up to the individual smoker to decide.
Tins with a few years on them, maybe up to a decade are good options. Ancient tins are always a crap shoot and generally an expensive one. If or when you are sufficiently advanced to swim in those waters, go for it.
Buying what's available and putting back enough to have some stock for the future is the best way to eventually enjoy (hopefully) aged tobacco.
The other fly in the ointment is that we're also going through a period of substitution and changes in named blends, such that the tin of aged "whatsis" was significantly different when new, then what's in the tin today.