Gary, I have done this technique in the past and would tell you it is extremely effective.  

We all have different strengths and weaknesses, so not every job or business suits everyone.

A lot of the answer to your question lies in being able to understand and maneuver the program to be most effective.

There aren't many options that provide the full suite of services (cleaning, guest communication, etc) you need to operate successfully. 

Why not use the CPI inflation to measure the effect (real prices)? 

Make sure you are taking the one best suited for you, given your risk tolerance, financial situation, and familial situation.  

The county/city zoning board has said this unit is not an issue and is grandfathered in, but he's worried about the more stringent FHA appraisal/inspection3) Buyer "skin in the game" - doesn't want to be left holding the property again as this has happened to him at least twice on previous land-contract/CFD arrangements4) Ability for buyer to acquire traditional financing at balloon5) Effective total cash to the seller is a primary driverWe submitted an offer that solves all these problems:Property A:Purchase price: 360k using FHA loan, owner-occupiedProperty B:Purchase price: 305k, 0% down, 25 yr amortization, 5 yr balloon, 4% interest rateNote + mortgage arrangement with professional loan servicing/escrowAssuming a 9% annual return in the stock market, this arrangement is equal in total cash to seller (including accounting for inflation,etc).

Hello @Michael Mendez,We use social media to market OHs but this has not yet proven itself to be effective... this could just take increased ad spend and consistency to be effective but time will tell.Our best OH marketing results come from reaching out to active Realtors in the area i.e. text/email blasts, phone calls.

I figure the stepping stone approach may be best suited for my game plan.

Especially with the eviction moratorium still in effect, I'd say you're better off making sure the property will be vacant at close or soon after.I don't know enough about sec.8 to tell you for sure if this complicates things.