My realtor recommended SDIRA Wealth, a company known for its high-volume new builds every year.

Sure, mortgage insurance eats into your cash flow a little bit if you're putting less than 20% down but in the scheme of things it's really not that much.Also, you won't have 20% equity in your property in a year assuming you put 10% down unless you are forcing appreciation or you somehow get some high market appreciation.

high cash flowing short term rental How did you find this deal and how did you negotiate it?

It is much more difficult to sell an entire portfolio that has become uninsurable (which would require a cash only sale) or that insurance rates are so high that no one wants to buy. 

And yes, attorneys make money from forming LLCs, but they make way more when you were negligent and didn’t know what you didn’t know and end up in a lawsuit. 

You’d probably end up with a bigger after tax gain if you sold the 2nd property for any amount of money and did that.

Your property manager should be supplying monthly reports and year end PnL reports that you give directly to your CPA. 

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

The payments and interest are high.

I’d love to get to know you all and hear how things are going on your end!