But I know how important cash flow is, so I appreciate the feedback on how the two are essential components to a good deal. 

This can be a very brutal expense to absorb if it were to happen, essentially taking all profits to fix.

That will get you familiar with all of the paperwork bits and overarching concepts without having to dive into renovations and finding tenants and property management companies yourself.

The notary will ask for it when paperwork is notarized, but never had the lender ask.

All in all, you can find a hard money lender if you are new to the game and dont have verifiable experience (deals where you are on the paperwork and not as a silent partner).

Specifically in Illinois, real estate services are "essential" and permitted. 

@Meaghan SimonichThe different pain points vary from commercial type.Retail- Depending on if it essential, a lot of retailers are begging for rent decreases or can't pay at all right now, and for retailers that do not have a internet presence, it is making it tougher to compete.Self Storage- Keeping the site updated -security, more automated features for tenants (Pay by app/kiosk, automatic gates, maybe more amenities on site (wash station, air hoses, etc.)Industrial- Longer lead time to find good tenant.I wish I could comment more on some of the additional commercial classes, but these are the only ones I have experience with.

one argument i heard against that was that if you basically have all the transaction done via 1 bank account, you essentially cant argue these are separate businesses in case of a suit   

Essential workers working largely from home.

Essentially its about having a game plan on how to get there and following it through cycles. 1031 is a great proven path way though.