It sounds so awkward, but that is what makes it funny.

Based on what you said it is likely that this person wants to help you with information, not with money, and asking for money puts them in an awkward position because you are friends.  

If you act awkward when you speak to people in a situation like that it makes them even more uncomfortable.

Over 3,000 sqft that originally had an awkward mother in law apartment and crow's nest above.

Over 3,000 sqft that originally had an awkward mother in law apartment and crow's nest above.

Things are seeming to break into 3 categories.a) "Working class" 4+2s that are really tiny bedroom 3+2s with poor garage conversions (so a random 4th "bedroom" off a kitchen, nowhere near bathrooms) or horribly awkward floor plans.

First we tried doing Airbnb with an extra room but eventually it got awkward with strangers in the house.

At first, the only way to describe it, was that the listening was a bit awkward.

I do all of my property maintenance myself so this will make for a very awkward situation.

They then suggest I sell my unit or get a roommate and then quickly moved on to another subject leaving me still standing up and awkwardly sitting down not able to say anything else on the matter....Luckily I was just using Airbnb to get additional income while I looked for my next deal, the condo does cash flow very well as a regular rental which was the plan all along.