So, who does...I've gone this far down the rabbit hole.

I've heard in some states it's illegal to give referrals to realtors that are monetary, including gift cards.

They get them selves stuck in a 20k hole and they try to dig them selves out by getting other people to join. 

Your plan seems to be over-simplified and has many holes in it.

Since Portland is such a tenant friendly city, I’m wondering if there is a loop hole or if I can choose the occupied unit to move into in an effort to rent the other at market value?

. - more so trying to build relationships and following the rabbit hole that leads us down.With regard to social media groups, is this primarily FB Groups?

After I close I will still have 30k in immediate cash and I have stock market investments that are another 30k, so even more frustrating that it's not even a monetary issue

Rotting window frames, unsafe electrical issues, a tub and sink that didn’t drain properly, a promised dishwasher that turned out to be broken and unusable, a driveway with tons of pot holes so deep that they could have easily damaged cars, and much, much more.

Good thing I caught their junk before I dug a deeper hole for myself. 

The probably of it being a worst case is generally pretty low.If you have problems under the concrete, get serious about breaking a hole.