Any time I assist anyone within my circle of closely affiliated colleagues, I always establish a compensation structure upfront beforehand to avoid any awkward conversations down the line unless I already decided to volunteer my time.

It is funny in that some have converted their attics to additional rooms and they have the most awkward ceilings, but they still rent.Hope this helps give some confidence.

Owner has kept up on maintenance and repairs overallConcerns - It would be very awkward to tell a guy that's been living in the unit for almost 20 years that I'm jacking his rent up $500/month.

That way everything stays within the business, and you don't have to awkwardly hold someone accountable for an unpaid bill (should that situation arise). 

She wants to be present when I show the Unit to prospective new tenants, which I think is incredibly awkward, and just wrong.  

I should have made it a couple feet wider so the walk in closet didn't impede on the space so much and make it look like an awkward layout.

This issue should be settled by the first phone call with them.That said, the conversation and process of moving on to another agent is still awkward.

In reference to raising the rents to market value, that is always an awkward scenario.

I on the other hand, am the nerdy awkward one who is better at crunching numbers than being a charming host.

It was awkward, but also taught me a valuable lesson.