I just attended the Bigger Pockets Conference and I discovered there were many books you can obtain through the Bigger Pockets website that might help you in your journey.

The biggest issue I observe amongst real estate investors is the inability to articulate the reasons why they should transfer properties or simply own properties from day 1 in an LLC.

Simply letting your mother live in the property rent free would make it personal property. 

So far I've discovered that we will need to acquire multiple permits and an STR license in order to legally list our property as an STR in the Baraboo, WI area.

While discovering these deals may be tricky, you may stumble upon a great and lucrative real estate investment if you know how to find off-market properties.What Are Off-Market Properties?

You are simply NOT operating correctly.

I don't think I fully understand using HELOC to pay points and holding costs only.Taz, that was my initial thought as well - even though it would hurt to get rid of a 3.5% interest rate, I could get an equivalently priced home with today's conventional primary residence rates and have about the same monthly payments that I have today, simply because of the HOA fees. 

If not, do you materially participate in the syndication or are you simply a limited partner?

He was born in kidney failure and later we discovered he has liver cancer.

Simply document your attempts to remedy the issue.