@Michael Taylor
You're wife's right about not buying in cook county. Why bother with the tax law, the horrible court process, and the anti-landlord legislation. If you find a steal there, buy it. You've got Indiana right next to you that's extremely landlord friendly and better cash-flowing, and wisconsin on the other side. Let's not forget all of the markets that are further away from you, which will force you to landlord without being present at your property (if you master this, you will thank yourself for investing the effort to learn it).
As far as timing goes, just bake the risks of the current market into your purchase criteria and find a deal that meets it. If you're worried about income, hunt until you find a cheaper deal that considers the current economic risks. Find a good wholesaler, or if you have the bandwidth try out a marketing campaign.
I've bought a property once a month every month in good condition for no more than 40% of its current market value since the start of everything Covid. I've got a substantial acquisitions engine in my business that makes this possible, so for you... set the bar at 70 or 75% of current market value, roll your sleeves up, and scrap!