Check local short-term rental regulations.3. 

You want to know the total demand and the existing competition.  

You'll find a ton of kind, supportive, and helpful people here.Are your existing 7 properties currently in Chicago? 

We try to keep good tenants for long term, an dhave several 30 year tenants and a 24 year tenant and average 12.5 years over the portfolio of existing properties.

These 6 items all can require a significant cost to remedy so it's important to be able to identify the existing condition.

I have a strong network here and know the key players/stakeholders in the community and am trying to learn how I can get involved to make an impact to change the community and restore the existing (beautiful) infrastructure. 

Navigating NYC's zoning regulations can be complex @Jon Pflueger, especially in M1-2 districts, which are primarily designated for light manufacturing and commercial uses.

Definitely look into HELOC/cash out options, but if those don't work in terms of rates or availability I'd suggest using the existing cashflow from your multi to offset a primary mortgage, and then find a primary with an ADU.

My question is ,is house hacking dead and to live rent free no longer exist in todays market ?

Selling some property to pay down high-interest debt is good, but also consider looking into ways to refinance or leverage your existing assets for better cash flow.