Quote from @John Warren: @Delroy Watson I would check to see if you can do this the "right" way and make it an ADU.

Bigger Pockets is a great place for education and networking and is full of great content.I recommend that you check out the following resources:1.

We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).

Check with your lender first—they may allow it if you personally guarantee the loan.2.

Bonus points if they’re used to working with investors or can help keep costs in check while maintaining quality.Cheers,Kevin I would say this about BRRRRR, especially as a newer investor. 

Check out the Short-term and Vacation Rentals forum.

You can setup a "guest mode" allowing the guest to enter their check-out date.

If you have a swimming pool check out the water pump system with aerial hoses.  

My recommendation would be to drive down there on a weekend and just check out the places you like and see the city before you dive in.

Make sure the lender you choose has a strong background in this type of lending...check them out on Linked In to see their experience level.