How capitalized are you (what is your ability to absorb big expenses if/when you have them like a major capex event)?

The other side to buying in almost all of CA right now is that evictions are not possible by any means, never mind rent control on top of it, but if you are adopting tenants in a 4 unit its not likely going to cash flow, and unless you have the ability to do cash for keys, and you have tenants willing to move then its another hurdle to cross. 

Happy to discuss what I've seen and the areas where people have found some success with some degree of mitigated risks. 

@Ry Eikleberry, The most critical component of success in any venture (and real estate is no exception) is your ability to draw a team around you. 

Even having a couple backup plans would help tremendously & increase your ability to make the best offer for you. 

Why are you even considering doing anything but your engineering degree.

I would start with your own ability to close first.

Do you host with AirBNB because of their fees and policies or their ability to get your unit rented?

So cap rates can be higher in the Chicagoland area, but you still have an ability to find new tenants if someone moves out... this is different from other markets which sell between $50-150/SF where you have significantly lower populations, so there are limited new renters in some markets.

If that happens, and you can act within that window to lock in a low fixed rate on a discounted property, it may be one heck of an opportunity (I'm thinking that's a few months out depending whether we have a second wave of COVID, and it might very well be location-specific, proportionate to the degree of economic carnage caused by COVID).