If you don't want the conversation to be awkward, you can just tell them you want to do more repairs and want the place vacant, or better yet have your PM do it, since that is what your paying for

The reason why I want to establish a rule early on is because I’m the kind of person that would let people use it for free but don’t want to back myself into a awkward situation.

Think of these high school relationships as awkward precursors to healthy adult relationships, but also realize that some people never get out of the teenage phase of their life.If you want to get a sense of their ROI, just spend some time hanging out with old people who have lived healthy relationships.

Might make for an awkward 30 days since you live there too, but it is what it is.I totally know how you feel because I started with a house hack myself, very similar to the situation you're in.

Before becoming ill, seller was rehabbing the home on her own, so there are some awkward tiling and flooring issues to be resolved, but she also stripped the basement as well.

Then the agent has to have an awkward talk with his/her client that they found the home they love at a certain price, but now they need to come up with another X% to pay the agent since the FSBO seller will not.A good agent will explain this upfront.

I get that it somewhat gives you two rentals... so yeah, there's that... but from a family perspective, I think you are better off not rocking the boat by putting your grandmother (and you) in an awkward situation.  

This will ensure everyone is comfortable with the agreement while also avoiding any potential damage that could be caused by attempting to move large, awkward items.

I think having so much turnover and churn with nightly rentals could create some awkward experiences and make some of your guests feel uncomfortable.I was close to offering on a place here in LA County a few months back, and my plan was to rent it monthly be the room on Airbnb, Apartments.com, Zillow, and FurnishedFinder.

They see a rent amount per month and then they call (gets awkward for them when I ask them if they smoke because in the HEADLINE of the ad it says no smokers.....and they go..."