I use Stessa for accounting, I love it, it links right to my bank account/credit card accounts and I can assign purchases to different properties and units of the property for multi-unit properties and at the end of the year I have a simple report to give my tax professional 

It is estimated that in 2020 alone $48 Billion was invested in new projects in over 3800 different census tracts.

Logically we keep telling ourselves, we have the experience to easily make the transition but mentally there's a big difference when dealing with 100's of thousands of dollars on a single fam / duplex and millions of dollars on a 20+ unit property.

In other words, if you don't fill your unit in the slow season because you're afraid it will cut into your high season revenue, will the high season revenue more than cover the difference?

I’m finally wanting to pull the trigger on getting another property, but this time the primary goal of turning the sfr into an Airbnb.

While to some extent software can act appropriately based on averages, that'd different than actually understanding the marketplace and workflows and optimizing.  

For example, if you’re holding a triplex in Irvine, the strategies are going to differ greatly from someone managing high-end rentals in Newport Beach.Costs and Terms: Watch out for hidden fees.

That being said, if this is a Heloc for an investment property and not your primary residence, most banks and CU's treat these as commercial LoCs, so the rate is likely be 9-12%.

As the 3rd largest MSA in the country it's hard to generalize the Chicago market as it's actually over 100 different submarkets when counting the 78 communities in Chicago property and then adding in the various suburbs, including in and around Naperville. 

No matter which path you take in real estate, surrounding yourself with professionals from different fields—contractors, lenders, brokers, investors.