Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

I'm not sure why that metric has held true but it still applies, the properties that perform well above that ratio are the owners that treat their STR like a business.

Then, if or when you decide to sell, you’ll have valuable insights to apply as you roll those proceeds into your next investment property.

It’s also important to consider if the work involved aligns with your lifestyle and goals.

There are variables involved, and there’s of course skill and effort required not just calls.

Might be good to apply to real estate.  

If they don't know how to screen and get the horrible tenant, they apply it to all.

I've heard that about the algorithm and changing your listings but didn't know about getting so closely involved with Airbnb + VRBO.

I would apply the cash flow to pay down the debt and hope to have significant passive income (or equity to put into something else) in 10 years.

These appraisers are too educated as in general this rule is virtually never applied on MF lots (I have heard of it once).