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. 

What loan product can I use to keep my current property , rent it so it can help pay for the loan while I build the second property ?

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.

Any help or suggestions will be greatly appreciated.

@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.

I want accounting, maintenance tracking and anything else that helps me manage the flow of my business. 

That would help your cash flow.

@Nathan Gesner@Kevin SobiloThanks both for the reply - very helpful! 

The journey's been exciting on my end, especially helping investors secure the financing they need.

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