For curiosity I asked Co-Pilot about it and got this response:The language in your CC&Rs stating that “no business or bed and breakfast is allowed” can indeed impact the interpretation of short-term rentals, but it may not be as straightforward as it seems.Definition of Business: Courts have often ruled that short-term rentals (like those listed on platforms such as Airbnb) do not necessarily qualify as a “business” in the traditional sense.

I’d prefer to avoid double-paying for insurance if possible.Additional Note: This property will be used as a short-term rental, which adds to the complexity.Any advice on how to structure the insurance to cover all bases without redundant costs would be greatly appreciated!

Unless you're direct to a seller, you'll often find yourself with a short pencil. 

Hey everyone, Has anyone done short term rentals in Chicago.

For those of you who’ve been in the short-term rental game for a while, what’s one lesson you wish you’d learned sooner?

If the appraisal falls short, I risk losing the deal and my $1,600 upfront cost.Any advice on navigating this would be much appreciated.

Depending on the tenant and what their financial situation is, you might also be better off giving them a 60 day notice and just telling them that you're planning to move into the property and do some updating. 30 days is usually too short for someone to have to move on, 60 days is plenty of notice for them to be able to pack and find another place.

I’m considering taking owner’s draws to recoup my initial equity in the short term but am unsure about the tax implications.

Rent should be a standalone line item.With regards to fees, these will vary from property manager--flat fees, % of rent, and other structures depending on short/long-term rentals, unit type and location.1) I'd recommend utilities be separate.

The main reason some investors put new STRs (short-term rentals) into service toward the end of the year is to take advantage of the tax benefits, especially if they have W-2 income they want to offset.