Advice on who I should talk to, to see if this is actually a deal worth looking into?  

(It’s actually something like pay the taxes that would have been due.

What I am looking for right now is a hard money lender that will do a cash out refi on this property because I have several deals in the works that I would like to close on.I am actually aware of a few lenders that can work within a leasehold situation, what is the current 'as is' value of the property?

@Caroline KnightI don't know the Chicago market but I'm highly supportive of house hacking.One thing to remember that positive cash flow isn't actually the goal of a house hack. 

From the initial notice to the actual eviction, this can be complex and time-consuming.

@Tristan Bennett, DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.Here's a bit more in detail about how rates are calculated for DSCR loans: 1.

Even the first thing in the actual Bill lists unpaid rent as collectible from the security deposit.As with everything that CA does to protect renters.

@John Mason the most important piece of what you are asking is what your comparable properties or "comps" show. 

It’s written for young aspiring investors just like you.I’ve actually read that!

While if you claim residency and then are actually buying things all over the area you really live, it looks more suspicious