My lender is great and super helpful!

I’ve signed up for Quickbooks to help with that. 

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

That would help your cash flow.

After coming from the Birmingham, AL market, I've learned that I really like to have a tight network of local investors who help shape how we're looking at properties. 

Can anyone confirm and if so, and local companies you recommend to help with removal? 

I also need a system that can help me manage my sales opportunities and pipeline, and is fully customizable to meet my specific business needs.I am particularly interested in learning more about how Salesforce can help with all of these requirements, including its integration with Google contacts, drip campaigns, and automations.

@Jay RitchieI came across this website which I think could help you: https://www.leadsafechicago.or...If you qualify for the city's programs, you may be able to get it done for free or at a discount.

For the past 5 years, I moved into short term rentals and Rob's expertise has helped me to become a better STR host. 

If you’re interested, I can help point you in the right direction or even introduce you to a few folks.