I’m hoping to find a great channel manager/PM system that has a great calendar functionality to sync with my owners calendars automatically.

But there are other loan programs out there - conventional (all major systems have to function), hard money, portfolio lending and FHA 203(k) rehab loans.You could minimize your losses by going this route. 

As has been mentioned earlier, the pet deposit is critical but also pet rent. 

I know this is a pretty long winded post and I still fell like I’m missing something, but I am wanting to glean as much information as possible from the experts here, so any other thought, advice and criticism is more than welcome.

They both have very stringent rules they follow on what the house has to have functional and up to date to pass the inspections and appraisal. 

"NOT" criticizing. 

If you narrow your search function to "Rent" on their website, you can see what properties in your area are going for.

Goals are critical.

Sometimes public sewers are available at the road and people don't hook into them until there is a problem (Why add an expense to replace a perfectly functioning system)?

The right/wrong LO can make or break your future success, so this is a critical step to find someone who is truly Team Alex and specializes with house hacking strategies.Once preapproved, your next step is to find a realtor who is also Team Alex and focuses on investors, ROI, the intricacies of Chicago neighborhoods, etc.