I would rather do lease options with an owner occupant rather than doing business with another investor doing the same thing I am doing.

What if right after he'd bought we had a big shock to the economy, and a recession with dropping occupancy?

Disgruntled tenants have no limits, and are happy to report your "illegal" anything, so make sure you're doing this by the books.And I'd advertise it as a duplex once the permits and occupancy certificate are granted.

Grats on your home @Christos Philippou.For context, occupancy fraud is the most common type of mortgage fraud.You're focused on the institutions in your post, but I'd argue in this case it's more about the folks you are working with.

What do they see them selling for per unit, what is the market occupancy rate.

Apartment properties around universities usually have high occupancy because the on-campus housing can be limiting and out-dated (unappealing to students) or in such high demand that some students just can't get in, so they turn to the next best option. 

Currently we track:  Vacancy rate # of tenants paying before 1st, 1-5th, 6th-10th, 11th-on# of Days a turnover takesAverage total length of occupancy.  

Typically, if your nightly occupancy is more than two standard deviations above the market average (200-220 nights annually) then you're under-priced and leaving money on the table.

His exit strategy is longer-term buy&hold.The goal is to structure a deal where we perform owner financing on a property that has a backing mortgage.I haven't talked to the lender about it, but was curious about whether, in this case, that was even possible.I believe our vibrant community here can provide useful perspectives, and thanks in advance If I understand the question correctly, you would go ahead and do the refinance to long term financing, (be aware that the note probably has a "Due on Sale" clause), you would meet the minimum occupancy term requirement, sometimes 6 months, sometimes 1 year, (read the agreement) and then sell to your buyer on a Wrap.

Since the houses will sit so close together we’ve positioned the windows so the occupants won’t be able to see in the other house.