I would love to find a mentor in my area (Belleville, IL 62226) and maybe find a way to earn some advice. 

If you can scoop up 190k of tax free gains (an option only available if it was your primary at least 2 of the last 5 years) that you can deploy doing some HML at 8-10%/year, that seems to br the clear winner vs the alternative of earning less than 1%.Your cash on cash should be calculated as annual income divided by original cash outlay plus current equity.

Weeks rented, revenue, costs, etc. so you can determine peak weeks/months as well as the rates.

Personally, as an investor prior to getting my license, my agents earned every penny of their commission.  

My dad used to call him "Buzz Baby" which my Mom thought would earn all of us a front seat in hell  :-)You can do a Google walkaround yourself, but I can tell you the neighborhood is poor working class, but not a crime haven.  

Meade the commute is going to be anywhere from 45mins-1 hour doing work hours, and 20-25 after peak.

We spoke about me earning my real estate agent license and my interest in investment. 

You might earn less.  

So I can see why he is more conservative because Nashville is reaching a peak. 

I would recommend reading as many books about real estate investing and doing as much research about it as you can before you get involved in investing hard earned money into real estate.