This will help you start building your team, learn a lot, and refine your criteria.Good luck and don't hesitate to reach out!

You don't need to know everything to get started; you need a foundation to build on and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

2) In a cash-refinance, let's say the new appraised value of the apartments is $1.8M, does this mean you can apply the $300k into the HELOC and not pay taxes?

When interest rates drop and you refinance, you'll see a positive impact on your cash flow.

I had an appraisal on a refinance recently, and I do enough business that I run into the same appraisers over and over again...so the appraiser asked me what value I wanted on the refinance.

If the interest rates come down, I can transfer the property back to my personal name, refinance, and then transfer the property again to an LLC or trust.Second and most important thing, I would like to get an idea of what type of property to purchase that best suits for STR in Chicago area , near by states like WI or MI also I am fine as long as it is closed to Chicago. 

So cash out refinance is my only option 

I just started to look at HELOC's, and don't think it'll be worth it to refinance because my low interest rate.

I'd find off-market deals, do some cosmetic updates, and then refinance. 

Underwrite your deal with new debt to see if it can handle a refinance/an increased debt loan.