Personally that is what I wanted, an active mentor. 

I get more responses from craigslist than this sec8 site.https://www.gosection8.com/logreg.aspx?

Quote from @Amanda Dobbs: Is there a place to find Private Investors as in one person?

and in response to your question about someone else - also difficult. 

I have a friend that owns over 60 rentals in his personal name and he's never been sued.

It sounds like you’re handling things well by setting up systems early.For this tenant, a calm and professional response is best to maintain a good relationship while reinforcing your policies.

I have arranged for Servpro to take a look at the property in person to give me a quote for this job.

I personally would stay away from condo-tels as they will be even worse and you'll have less opportunity to cash flow. 

Do you rely more on the deal itself or the person behind it?

I call it that because most commonly the listing agents call me and says "you mother f...." to me in response, lol.