He pays what you call regular income tax PLUS 15% self-employment tax (Soc Security/Medicare).

I assume you have a security deposit?

Yeah that makes sense on a larger property there are economies of scale so hiring security cost per unit wouldn't be as expensive. 

Is there a security deposit? 

We do have a secured solid wrought iron fence/gate to the alley, so the tenants are secure as long as they remember to lock the gate.I will go ahead and try to contact our council member and see if anything sticks there.

The handyman demand here is INSANE— everyone worth their weight is booked for weeks.

Your friend should send a demand letter for the return of his security deposit, or whatever portion of it he feels should be returned.

We do have simplisafe which might have failed to ring.My idea is to have a security guard who can be present at the property while no one is working there.

Roughly speaking, my mortgage payment would deflate (reducing my "rent payment") or if I rented it out the rent increases would inflate, keeping the previous numbers "real."4)  Social Security @ age 62, $1,760.The above scenario does not include my taxable account of  ~ 110K, which is about 15% stocks, 10% bonds, rest high yield savings cash.  

Did you collect a security deposit to assist?