Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

I have found someone that has great income and can really afford to stay in the home. 

So make sure he’s got enough coming in to cover that.)Don’t forget your property taxes will probably go up, and he should have renter’s insurance.More difficult if you have siblings to make sure everything “stays fair.”

@Scott Trench - have you considered investing in short term rentals, materially participating, and having the average stay be less than 7 days?

I am purchasing my first property and I am deciding whether I want to rent it out and get a cheaper apartment or stay in it and pay the mortgage myself. 

Or do i stay where im at?

We haven't stayed as guests for 2 years.

This was loud enough for the other tenants to hear which made them feel uncomfortable because the environment now feels hostile and unsafe.Unfortunately, all this started happening when I renewed the lease, which means this tenant is going to be here for the next 11 months and I am obviously not renewing it.My other tenants are very concerned for their safety and I’m seeing on the cameras that this section 8 tenant is having people over every single day.

They actually mentioned in the review that all the rest was great and that they could even solve their perceived uncomfortability issue by using cushions, which we have a lot of.

Without clear guidance from the CRA or definitive legal precedent, this remains a gray area, but it’s worth noting that we have not seen CRA challenge this structure in practice.If this potential issue makes you uncomfortable, there’s an alternative structure to consider.