Algorithms that get harder to solve with package size

So i think you folks are probably the most informed about crypto so ill pose this question to you.

I didn't plan on relating this to crypto currency since its not for that, but i will try to lay out an example that aligns so maybe i can get some suggestions on feasibility.

Lets say that i am asked to issue an encryped package (coin) to someone... so i create a record that consist of payload plus thier address and from that i generate a hash. They then give the coin to someone else and tell me so i start a merkle and hash again with the new address on top, and so on so forth n number of Times.

What i want is for the final stop in the chain to be able to undo all that hashing and supply me with the original encrypted data string.

Yes i know this is basically like breaking weak ciphers, but it should be completely solvable. Not based on guessing but actual math that just takes a while.

The difficulty would be controlled by the length/size of the package, and the layers of hashing. (Both known values)

The end goal is to show proof of possesion and originality without knowing or caring what data was actually encrypted or packaged. So at the end not only must the hash they ended up with match my records, but the encrypted data they send back must also match when i decrypt it.

Any thoughts? Im sorry i cant explain this better. I only have a loose picture in my mind of how this would work.