Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

I've also used some more obscure companies in the seller financing world like Pioneer Title in Idaho (they call in Long Term Escrow Servicing) and Security Escrow in NM (recently purchased by Sunwest Escrow).

Basically, the demand is much weaker than the supply. 

Sometimes it can be difficult to collect and some landlords will keep any unpaid utilities out of the security deposit, though CA is one of the trickier states to do this in.

Looking ahead, once you secure a tenant, perhaps this is something that should be explored to make the next lease up easier.Also, @Caria Mitchell raised an interesting point in saying: We are experiencing a shortage of qualified applicants, I’ve noticed non-conventional applicants vs qualified applicants that don’t have a voucher or some form of subsidy. 

With your point, it seems like living security of 'where's next' for them will be the biggest obstacle for the seller to overcome.

I guess my challenge right now is to define the strategy and balance all the factors, such as job and population growth (value increase), cashflow (demand & supply market, interest rate, property tax, maintenance cost), and risk control (insurance etc). 

He isn't rich enough to have a body guard and a security professional.

"TaxMaster 2023"   :) We have supply chain issues in our country, not he least of which is a shortage of truck drivers.Flipping through tiktok (hold your laughter until the end, please), guess what I saw on tiktok "live," with THOUSANDS of viewers? 

It seems like offering this as a separate package once you secured the booking is a good idea.