Asking about the SW suburbs specifically, in the land of long sidewalks and big actual parking lots. 

The specifics of your situation will determine where you might need to fall on that spectrum of holding period.

Networking, local meetups, door knocking, mailers, wholesalers, online forums specific to your area of interest.  

I wish there was a system for searching for STR specific things but I have only found something like AirDNA to be the closest even though it's far from ideal for that.

And are there any specific permitting issues popping up post-storm?

Have you explored specific neighborhoods yet?

How can we prove that any damage is caused by this specific tenant, given multiple residents in the property?

It’s good to budget for unforeseen expenses.Regarding PMI, it’s worth discussing directly with your loan servicer since many lenders require holding the property for a period or reaching specific equity thresholds before removal.If market rents are $2,200–$2,500, hiring a property manager could help you optimize rent while taking the burden of tenant screening off your plate.

If you have specific questions about property management, I'll be happy to help!

I was just reading Mark's book "The Tax & Legal Playbook" this morning and it specifically had a "critical warning" (page 31&32 in Chapter 3).