Interesting analysis and topic! I currently have a commercial land development property on the market and am currently offering owner financing. The reason I am offering this is to make a sale easier and close of escrow faster for a potential purchaser. What I would do with the sale proceeds, as pointed out in your post, is reinvest in a first deed private money loan anyway. Why not make an interest return on this property right away, which I already am familiar with and favor, without having to find another property to re-invest the sale proceeds? A few terms that will make this owner financing work for me as the seller: 50% down on the purchase price (it is raw land fully entitled and permit ready to build) and taking the 1st deed position. I can offer an attractive interest rate for my borrower that we are both happy with, and zero points to originate the loan - also beneficial for the buyer. As with all first deed trust loans, my rule is to only invest in a property I wouldn’t mind owning in case of default. Worst case scenario, I own the land again, have paid off my note on it, and made interest income off of it. That is why owner financing is very attractive and favorable in this case for me as the seller.