If you are going to move forward with this deal, you’ll want to have a review of HOA financials.  

Tenants like to set up insurance, show proof to the Landlord, and then immediately cancel the policy after moving in.

In fact, for tax sales in PA, the parcel number check is usually best performed first, to see what mortgages can be found (if any); seeing a big mortgage means it's best to move on to the next property on the list.And on a side note, IRS liens can be wiped out at foreclosure of any kind, provided the IRS lien is in a junior position and provided that proper notice is served upon the IRS. 

Off-Market: I was working for a storage facility and the owner needed help removing his stuff because he was moving How did you finance this deal?

We know 3 of the units can't be the issue since they either moved in or out while this was happening. 

Keep moving forward and if you ever need advice, just summon me here in the forums, tag my name and I will answer your questions here in public.

2.The best way to obtain the necessary permits and ensure compliance moving forward?

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

This helps the process move much quicker on my virtual deals.

Everything on my side was set to close, and then today the seller is refusing to close on Monday as they have not moved a few pieces of furniture they were supposed to get movers for.