Where you might be disappointed is if you like "extra mature" British cheddar, which is not really equivalent to "extra sharp" American cheddar. Personally I find both unappealing.
For cheddar specifically, yes, I'd hesitate to buy anything younger, and if I had to I'd only use it in cooking.
Maybe that partly explains my experience/surprise, but a sibling comment shows photos which though not close-up seem much more like what I 'expected', or rather was surprised to notice an apparent lack of.
https://i.imgur.com/WWOuGGW.jpg
https://www.theneighborhoodmoms.com/wp-content/uploads/2014/...
https://s3.amazonaws.com/spoonuniversi-wpengine/spoonunivers...
https://www.mcall.com/resizer/TMbbZ3l7Ik9C7bvyY7rc6Kce43c=/1...
https://s.wsj.net/public/resources/images/BN-RZ602_NYCHEE_P_...
(I didn't mean the first part as a claim to expertise; the second was a genuine question.)
I noticed "Fancy cheese" (not velveeta) showing up regularly in the 2000s, when I was starting to shop for myself, and as my cheesy experience grew, "good cheese" like the better stinky ones were more available probably 4-5 years later. Now, even in my local supermarket which is considered the "worst" of all the grocery stores in the area, I can get authentic cheeses from a variety of places.
I don't think people's tastes evolved as much as the supply chain for getting these cheeses around has improved much in recent years, making tasty cheese super affordable.
Most British Cheddar isn't from Cheddar either.
And there's plenty of really good mature Canadian Cheddar for example.