Great job turning your condo into a cash flowing asset! 

I have not run into that yet, have you contacted them to share with them this misinformation?

In digging into the details through public record searches I find out that he has had 3 evictions, several drug convictions, and a violent crime.

Say you need a new roof, or a new boiler at year 28 of ownership......does this turn into repairs/maintenance? 

I do like the built in leasing that apartments offers over the OG Cozy site, but I don't really want to pigeon hole myself into the apartments.com brand (or Zillow, or any other of the type) so I'm starting to use rent redi.

Assuming I get an appraisal of $500K, I have ~$110k (75% of appraised value minus the loan) I could tap into for equity for a HELOC.Question: What is the process for getting a HELOC?

I can say that with Phoenix, a multitude of opportunities can be in store for you if you invest in their market, network, or even just want to get familiar with it.What type of real estate are you into: fix & flips, buy & hold, multi-family, or something else?

For the second property, I would expect to have to put money into it in some fashion.

That's $1680 per year for QBO, plus my Bookeeper at another $500 a month to log monthly statements, break down loan payments, and reconcile.

Factor it into your cost and decision.