It’s humbing and frustrating, but it also teaches you those guardrails you’ll want next time.. like thorough screening, a solid lease agreement that sets ground rules upfront, and maybe even setting aside a bit more cushion in reserves.Chicago’s got plenty of investor-friendly pockets.

It could provide more cash flow but your leverage would still be less due to the total value of that property compared to the 4plex3) Is there an easy way to understand what price range I should stick to in my area, and should I focus on the best market or focus on the best price for properties? 

I have actually seen this before and courts usually stick to the rule unless you get dam lucky. 

Rules are super landlord-friendly and we see positive cash flowing deals with lots of potential for appreciation.

Note I strive to minimize cash flow because it gets taxed versus other RE return are easy to defer or avoid the taxes.  

That's easy compared to trying to fight and erroneous $13k water bill (a real issue we had) or an insurance policy tripling (that too).

With regard to the proximity to the beach, I tend to have a beach distance of 15 min or 5 mile rule, whichever is less. 

But as said above it is not an easy job and the salaries are not great working for someone else. 

Things like the 1% rule right off the bat, especially with properties that I know are undervalued, are good indicators of a "good deal."  

The process is easy:1) You’ll receive a disarmingly simple one-inch-thick three-ring binder containing your plan documents.