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Technically you could have 38+ Dragon Riders where I am (and I'm not all that close from the final battle), which shouldn't be too far from what's available from Leadership.
Is it possible you missed some?
From there, you open up an option at the school in Inselburg; when offered 5 princesses for half a million gold, you can refuse and instead ask for 10 almost-princesses for the same cost. After you buy them, you can buy the real princesses.
That's a million gold for 5 real and 10 false princesses (15 total).
When you've turned in a few princesses (hopefully false ones) to the dragon, Marie Curie has the False Princesses option. You have to turn in a real princess to complete the questline but you get 20 False Princesses from it. Total: 34 princesses (4 real 30 false).
You get a real princess in Dragandor, and you can get 3 more in the sky island. Total: 38.
There's very possibly more princesses elsewhere, I just haven't found them or gotten to those parts yet.
I play the high-Leadership class (Demoness) and I have the rank III medal for hiring female units (-20% Leadership cost) so I can hire a *lot* of Dragon Riders... and I can only hire about 27 or 28 of them. I might very well get to above 38 before I finish the game, but just barely.
I was somehow sure that false princesses were made of common females by Feline, with the help of reproduced dwarven princess dress. I thought that I may come with any number of common females and have them converted to false princesses anytime after completing the quest... Seems not.
Yes, unfortunately the false princess quest is unrepeatable.
You probably missed the 10 false princesses from the charm school? They're tricky to get because you don't see the option until you've been offered (and have refused!) the 5 real princesses, and when you do buy the 5 real princesses you can't buy the 10 false ones anymore because the NPC leaves.
If there's three more princesses on the Amazon island then it all adds up to 41 possible Dragon Riders. I doubt many people have the capacity to hire much more than that.