What neighborhood of Chicago and how large are the buildings?

Just no guarantee if things get better or worse in your neighborhood.   

Indianapolis and surrounding areas often offer strong rental demand and reasonable property prices, so you’re definitely looking in the right place.For neighborhoods in Indianapolis, I’d suggest checking out areas like Fountain Square, Bates-Hendricks, and Irvington.

As you can tell marine the appraisal came back 40k low and I was so dumbfounded.  

.🎯 Your 6-Month Timeline:Month 1: Foundation (5-7 hours/week)Morning routine: 1 hour daily market researchEvening routine: Deal analysis practiceWeekend: BP forums & networkingKey Goal: Analyze 10 deals on paperMonth 2: Education (8-10 hours/week)Complete 1 RE courseJoin 2 local REI groupsSchedule lunch breaks with agentsKey Goal: Build your initial power team listMonth 3: Systems (10-12 hours/week)Set up deal tracking systemCreate document templatesEstablish banking relationshipsKey Goal: Ready to make offersMonth 4: Lead Generation (12-15 hours/week)Drive neighborhoods after workWeekend open housesSetup automated MLS alertsKey Goal: Generate first 5 qualified leadsNow, the Owners and Brokers you deal with may not enjoy this, but you can certainly "practice" making offers.  

note if we sell the primary residence, it is very likely we will not need mortgages to buy smaller rentals as we would use that mostly.Though I take your point on keeping it. our house was a new construction (3 years old) though so possibly low maintenance risk to keep for a rental. 

Congrats on your lot purchase in an awesome Chicago neighborhood like Humboldt Park.

I don't work in Nashville area but $165 per sq ft seems quite low to me.In terms of financing, I would speak with a few construction lenders and also hard money lenders.

When loans were called, was it due to specific triggers like delinquencies, insurance lapses, or low-interest rate portfolio loans held by smaller banks?

We are not likely to see rates that low again in our lifetime.