Do whatever you can tied get him to sign the extension or at least get a written statement from him saying he agrees like email or text.

If you haven’t given him the $5000 you don’t have an agreement for an extension anyway.

The dilemma is whether I should hold more of them instead for the added benefits of: appreciation, tax benefits, and amortization since I don’t need the flip income to cover my personal and business expenses and I’d have none of my own dollars invested.

Going forward it is not that different because you would be increasing it from 27.5 years to 30 years under ADS.

I plan on telling him I am ok with the switch, provided the new tenant is added to the lease, the new tenant passes all the usual screens.

Google Earth down to all the commercial shopping 1-6 block radius, look for boarded up windows, broken windows, Grafitti, types of cars, types of people, trash etc... if you see all of the above.

Currently listed at 65K with not many comps around but a similar 4 bed 2 bath a few blocks away listed at 62K.

Consult with your tax professional (CPA, HR Block, etc.) for the exact definition of these and what you should do. 

This one thing is a stumbling block for me.

If you can put your money into an asset that is growing at 5-7%, and you can get a line of credit against that asset at Prime, then anything you do with that borrowed money that earns more than Prime is adding value on top of the dividend/interest crediting rate of the cash value in the policy.