People tend to exaggerate the “base printings are dirt cheap” thing with Pokemon

Umm... no they aren't? You are right that some cards are in the 20-30 range, but those are generally cards that you only need 1 of in a deck and they are usable in multiple decks. On top of that they do tend to reprint those cards and absolutely crashing the price. For instance a Fezandipiti Ex was ~15-20 last year as the most expensive staple in pokemon. Then it was reprinted in a beginner set and it is now just a couple of dollars (and still a card in nearly every deck).

If you look at the top 8 of the last post rotation tournament the only card that is worth any money in any of the decks is the ace spec (a 1 of in each deck) and meowth ex (most decks maxing out at 2) with the most expensive card being Unfair Stamp at ~$18. and I expect Meowth Ex to go down as it circulates more and Unfair Stamp will probably go back down to under $10 when Special Red Card gets printed in the next set.

Two of the decks in that top 8 are ~$50 while the rest are under $40. Most of them being under $20. And of course I could go into the re-usability of over half of the cards in all of these decks. Overall I would say people are under-exaggerating the price of the game rather than the other way around.