Underwriter I respect told me a lease option is just a forward contract where one party forgot to hedge
That landed on me hard this week and I have been sitting with it since Tuesday. He said it in the context of a deal I was looking at in Akron, $187,000 strike, 24-month term, seller wanted $4,500 in option consideration. His point was that I am pricing today for a delivery two years out and I have no position on what rates do between now and then, no position on whether the tenant-buyer qualifies at month 22 versus month 14, and no hedge if the appraisal comes in at $174,000 when the tenant-buyer needs $187,000 to close. He said a futures trader would at minimum know what their exposure is. Most lease option investors, his words, do not even frame the question.
I killed that Akron deal at the spread the same way I have killed twelve others this year, but this framing stuck with me in a way the usual cap rate math does not. Because he is right that the risk is not just default. The risk is that everything goes according to plan and you still end up with a deal that cannot close because a number moved. Tenant-buyer performs, pays on time, saves the credit, gets to the finish line, and the appraisal or the rate environment or their debt-to-income at that exact moment kills it anyway. All the option consideration you collected does not make you whole on 24 months of below-market rent if the exit never materializes.
I do not know what the clean answer is. But I think I have been underwriting tenant-buyer credit paths and not underwriting the forward price risk at all, and those are not the same thing.