These are being issued by local "nonprofits" who are mass emailing landlords pretending to be section 8 tenants.

Now I can see some builders having an issue with comps.. but other than that its crazy to take these funds as income and then pay tax and plow it right back in.. 

I am remembering a lawyer friend advising her parents on land issues.

The issue why most wives don't like this strategy is because they have to move into an ugly home that will be a construction zone for the near future and they have a hard time looking past that.

You have a number of issues in your post unfortunately.

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.

For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest?

Tenant is now saying that she’s in a hotel because the issue is getting worse and that the apt has had roaches for “years”. 

I have done it in the past and never had an issue until recently.

Basically, "wholesaling" is no longer permitted.