A related-party lease priced like arm's length rarely survives buyer diligence
Take a small town case, population about 4,200, an hour from anything. 11,000 sf building, half storefront retail and half warehouse, three tenants. Rent roll shows $86k gross, expenses about $24k, landing at $62k NOI. Contract at $690k, a hair under a 9 cap. Plan is to assign around $735k to a rural buyer. The seller occupies 6,000 sf of it with his own business at $9/sf triple net. Everything else in that town leases at $4 to $5/sf if it leases at all, with two empty storefronts on the same block. The seller had signed himself a ten year lease three weeks before listing it. A buyer running real diligence strips that rent to market on the first pass. NOI goes from $62k to about $41k. At a 10.5 cap appropriate for a tertiary market with no depth, that's $390k, not $690k. The tell shows up when the buyer asks for a personal guarantee from the seller behind that business lease and the seller refuses. A second buyer's lender may not even get that far, since many lenders won't quote a building where over half the income comes from the seller, though that policy varies by lender and is worth confirming directly. A deal built on an unmarked related-party lease commonly dies well into the process, often with several thousand dollars in earnest money, travel, and third party reports spent along the way. The lesson: any related party lease should be marked to market before a contract is signed, full stop, and the guarantee question belongs on day one rather than something a buyer discovers later.