What I don't understand, is why someone would be willing to buy 15 medallions at an "inflated price." My point being, you should have some basis on the PV of cashflows you can generate with each medallion. It doesn't seem like an extremely complicated financial problem in my eyes. At some point, you're cutting into any investment return you receive through cash flow and you're now expecting your returns to be generated through the appreciation of the medallion. That's probably where I would stop and think, I don't need to buy 15 of these things.