Rental activities qualify if they constitute the conduct of a trade or business (see IRC 162), or meet a rather awkwardly structured safe harbor activity requirement.

Needless to say the work environment will now be pretty awkward lol.

When I first talk to someone I feel like I am terrible awkward but as soon as I get past the beginning I am fine. 

It sounds like you are a go getter which real estate is perfect for that, but it can be a very awkward transition if you don't just dive in.

You will always run into the problem of having to make that awkward call or email when you accept multiple applications for one unit.

Talk with her now about it and you will avoid an awkward moment later.

I've been to Ultimate Partnering and thought it was much better to be outside of the conference room talking to other investors than actually sitting in the event listening to the awkward sales pitches.

Several architects, my friend and I all agree that the layout of the home was designed very awkward and not very well thought out. 

This is my first time as a landlord and this makes for awkward circumstances but it is also a business and not a charity - where do I stand? 

It will protect you from a liability standpoint and as you say it'll make sure you don't face that awkward conversation with a buyer later down the line.But your original post suggested he calls the city out right away.