I am definitely open to seller financing, I just wanted to have a back up plan if we decide on this route and we cannot find a seller willing to carry  

Secondly, you'll definitely want to confirm with a tax strategist with experience in the STR space to confirm if the setup you describe will pass as an STR with the IRS. 

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Also, if your unit was not previously listed within the year at a specific rate, you may definitely be able to list your unit at what the market is currently.

It may be a tough pill to swallow if you feel you’re totally right, but you may be surprised at the LEGAL opinion rendered by counsel.  

There’s definitely a place for both, and I don’t blame anyone for wanting to save a few hundred bucks if all they have is a W-2 with no plans to invest or start a business.But let’s be real—life isn’t that simple.

I won't be able to make the cottage legal rental without living in the primary home myself.

Tax and Legal ConsiderationsUnderstand the tax implications and legal responsibilities associated with rental income.

Definitely in support of @Todd Anderson's reply above.

In Illinois, when an agent does that, there are functions normally expected of the realtor that they are legally prohibited from doing.