So we stood back quietly and awkwardly while she hauled the content of the living room out onto the lawn and then into the back of her truck.

I think it would be best to give your condolences but then its awkward when the old resident is just moving to a retirement home.  

I've managed a building just two blocks away, with a more awkward layout, and everytime I tried to rent it, I had more calls than I could deal with and 3+ applications submitted (with credit reports) within 1-2 weeks of posting the vacancy. 

Well I just took my first ever direct mail call and it seemed a little awkward haha, in the sense I feel the call was just to be taken off our list.

I bet that was an awkward conversation! 

I know it's awkward trying to find someone that will teach you the ropes, but offer your time to them and work for free if you must.

Too often, today's "great deal" becomes tomorrow's awkward Thanksgiving discussion topic.

I want to avoid the awkward, weird situation of walking multiple contractors through each unit and discussing the changes I want to make while the tenants are present.

@Pavan Sandhu - Considering they will be a mix of short-term rentals and long-term rentals, I think it would just devalue the upstairs bedroom a bit because it's awkward.

It's about as awkward as walking up to someone and asking, "Will you be my friend?"