Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

Sidenote: if borrower is paying P&I and investors receiving interest only it gets more challenging as you are receiving dribs and drabs of principal back every month which is impossible to deploy but you are still paying investor interest on it. yup drag on the fund will drag you down.

Given that I utilized that $200K to buy over 18 units, the cashflow I received from those units far exceeded the interest on the HELOC.

Principal balance currently at 314kProperty Details: It's essentially a "2-in-1" property, with the main unit rented out for $1,900/month and an attached ADU bringing in an additional $1,200/month.

My goal is to live in the home during the winters, maybe 3-4 additional weeks for vacation, then rent it out to help cover the mortgage the rest of the year.  

Put the answers together and post on Classifieds Forum.Feel free to post answers here for additional constructive feedback:)

Both properties have a substantial amount of equity that’s essentially sitting idle.Would it be a good idea to tap into this equity (through a HELOC, cash-out refinance, etc.) to fund future fix-and-flip projects or purchase additional rental properties?

I have received mixed information regarding this!

There is no additional "risk" on the note like a demand clause etc, but you have  extra expense in upfront one time costs and the pre-payment penalty that most programs are sold with if rates do drop as expected in the future.  

We found two contractors and the bid we received to finish the work were higher than the bid we contracted to complete the entire rehab!