What makes a stamp expensive? Commemorative stamps
It's not often these days that the United States Postal Service prints stamps with the exclusive purpose of them being collectible. In fact, they, along with the Mint, are pretty darn insistent on preventing anything special, misprinted, or otherwise collectible for its rarity escaping their production lines. This, of course, only results in misprints becoming the absurdly expensive coins and stamps for their rarity.
The USPS does still do commemorative stamps, of course, but they're still made with the intent people are going to stick them to letters, and they aren't sold at a big markup over regular stamps. Or any markup at all, now that I check, at least for 'Forever' stamps.
Anyways, that point is that they used to, back when it was called the United States Post Office! Commemorative stamps started in the US with the 1893 World's Columbian Exposition as a fundraising effort for the Post Office Department.
By issuing special stamps for the Exposition, they'd hoped people would buy the stamps and then not use them, thus giving the Post Office money in exchange for basically a souvenir. The full set had 16 stamps, several of which weren't even in the right denominations for mailing.
The most expensive was five dollars, or $167 in 2023 money, and the full set would cost $528 today! Despite that absurd cost, the Post Office's stamps were a huge success for them.
The souvenir stamps pretty clearly had their non-usage in mind. They were printed larger and with more elaborate art than a comparable stamp made to mail.
The cost made a lot of people in the budding stamp-collecting hobby rather upset. One result was the founding of the Society for the Suppression of Speculative Stamps, the purpose of which was to protest these frequently-made high-cost collectible stamps, since anyone trying to get a full set of US stamps would now go bankrupt.
Well, the Post Office wasn't deterred because they raked in money. This leads us to probably the most famous example of a commemorative stamp, and it involves zeppelins! Not the Hindenburg (this time), although that certainly didn't help.
The particular zeppelin involved in the downfall of expensive commemorative stamps was the Graf Zeppelin, actually the second airship called that. This one was sister of the Hindenburg and nearly the same size.
You may think the biggest problem with the zeppelin program was that they used flammable hydrogen instead of helium for a lifting gas, but coming in a close second was that every single aspect of them was extraordinarily expensive. This was made worse by their heyday being also the heyday of the Great Depression right around 1930.
The Graf Zeppelin was literally expensive just to look at: they charged tickets to see it from the ground. Among its financing schemes was a transatlantic airmail route, something quite rare in the early 30s.
The Luftschiffbau Zeppelin and the Post Office thus entered a partnership: The Post Office would create special stamps which could only be used for zeppelin mail, and it would also give a large cut of the income to the zeppelin company.
There were regular stamps that would send your letter across the ocean, of course, but one of the set was rather unique: For $2.60 (~$47 2023), your letter would go across the ocean... and then right back to you. It'd receive a special franking stamp! Perfect for collectors, useless for everyone else.
The Post Office expected much the same results as the 1893 Expo where people would buy these for the sole purpose of collecting and investing.
Unfortunately for the Post Office (and Luftschiffbau Zeppelin who would develop much bigger problems by 1937), people were a bit too broke in the 1930s to spend 50 times the cost of a loaf of bread on a collectible stamp. Barely 7% of the three million stamps the Post Office printed actually sold, and the rest were recalled and destroyed.
Funnily enough, that makes a 1930 Graf Zeppelin stamp today incredibly rare and expensive! Go figure.