We should have been more diligent about implementing late fees, but honestly it just felt a bit awkward since we live in the building as well and see this tenant around the property.

Very awkward.

It's never been weird or awkward.  

I will state though that wholesale chaining can work when there is an understanding of what is happening but most people prefer to say I'm sorry rather than ask.As I stated in my first statment its not that some investors are unethical (these can all be legally done) I would argue its less ethical due to an individual not being transparent and trying to put people in awkward situations where they are exploited.Sorry for my long rant I hope it made some sense. 

I picked up the properties for a heavily discounted price (because they had sat on the market), and had no problems finding highly qualified (and high-earning) tenants that made the place cashflow right out of the gate.Another example: I once bought a property in an A class neighborhood that had an awkwardly-placed stairwell inside the front entrance, which turned off other buyers.

This allows the small, attached "dining area" to fit a small/medium table w/ 4 chairs, instead of having a large, awkward fridge over there, and eating at the coffee table in the living room..

I thought of that, signing both sides would be awkward.

This way, it doesn't put you in an awkward situation.  

It doesn’t work in a forced awkward situation.

It actually looks weird and awkward to me... the window shadows are still there even though furniture would be blocking the space.