We both own 1 property at this time. 

I would suggest starting with reading the IRC book all the way through multiple times.

I have owned it for a very long time and had depreciated most of the original purchase price. 

One of my applicants showed up with little credit but no defaults, no evictions, and only traffic violations and verified income high enough to cover well over 3 times the rent and I accepted the tenant despite there being some signs.He paid the rent in time for the most part until a few weeks ago when he stopped and I could not get ahold of him.

I have an available and reliable contact in Chicago, but am concerned about that time window.

Rent in full on time every month with little to no turnover/vacancy. 

When I go to events like this, I do go to some of the sessions, but most of my time is just sitting in the lobby chatting with people. 

If the property was in Hartford proper, we would tell you no to management since the tenant base is much harder, it is harder to get rent collected on time.  

Good morning BP community,I'm a returning REI in East Tennessee who is now investing and buidling a family business full time after a career in the military.

You'll always have the luddite stragglers but it's the response time that matters, not the avenue.