Chicago taxes are no joke, glad you are able to take advantage of the lower taxes in Will county.Would love to hear how this deal pans out....you got to make it happen!

I wanted to park some money into RE as I had some in stocks, crypto and found that RE has many tax advantages as well as monthly cash flow in addition to principal pay down.How did you find this deal and how did you negotiate it?

Because knowing what I know now, I would have liked to put in appraisal contingencies with my offers.Very confused and starting to think my agent is taking advantage of us.

At the end of 5 years, I would technically be $21,500 'richer' on the balance sheet due to the investment, as well as $50,000 added additionally to the balance sheet from repayment of the loan from my W-2.I'm literally taking money out of a tax-advantaged account that I can't touch until retirement, without fee's and penalties, and using it to invest in cash flow assets that I will get back at the end of the investment period. 

There is no reason not to take full advantage of such a fantastic loan product. 

When working for yourself, buying BRRRRs, Flips, STRs, Etc, there is no advantage that I am aware of.

@Jeremy Nault HELOC is a line of credit and that creates advantages, but you could just do a cash out refinance on the property.

I have a female tenant who is moving in in two weeks and she's asking me if I plan to put up blinds.

Getting started so young is a huge advantage.

You will be living here and utilizing the advantage of your high appreciation market, compounded with quality leverage from an owner occupied loan.