They made an attempt to pay me $500 for 3 months as interest, but haven't paid me for awhile now.

Does anyone have experience trying to refinance a multi family commercial loan with Fannie a second time on the same property, after the first attempt failed?

Tenants will then proceed to trash the property in an attempt to justify their claim.My question is how do you get proof of a habitable environment during tenancy and how do you prove that your property is habitable before the tenant trashed it?

I do std rentals but you proably are right about airbnb as long as Austin doen't enact STR regulations or limits.   

While it is possible for me to reach my goal with option number 1 (slowly collecting rentals), do you see any upside to attempting option 2 (flipping to collect capital to reinvest into rentals)?

We attempted to see about changing this and talked to Auditors office and one thing we ran into was a parking ratio constraint.

After my first attempt to personally contact the owner/listing agent weren't taken serious, we got ourselves a local realtor with rental-property experience who had a reputation for staying on top of things.Offered full asking price.

A program like this would help ease all those tensions, turn things around.It looks like Path to Ownership was an attempt at this but didn't involve landlords? 

At this point he will take over all comms with the tenant and receive any payment if they attempt to pay.

Maybe make one last attempt with a friendly phone call, then move on.