I see many houses a duplexes that have awkward window A/C installations.

It is unfortunate that him and his family only enjoyed the new AC for one summer and we are put in this awkward situation. 

I feel if I can find a way to feel less awkward about it, I can get over the mountain and actually begin investing much quicker.

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.

@Bud Gill I also wonder about investment companies like Blackstone sweeping into town and buying up thousands of homes to turn into rentals.

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.