He shares my concerns about the insurance, capital reserves, resale issues, etc.  

If the market dives when you are halfway through a flip that is taking 2 years when you thought it would take 6 months you could have an issue on your hands when trying to resell.  

Chicago has had a lot of issues  and they seem to be getting worse.

I know the issues and we are addressing the issues. 

One issue you'll likely run into is even getting conventional financing in the first place.

He also told me the fly infestation were bottle flies and were a sanitation issue.

The two biggest variables are condition of the condo to begin with (ie. if it is old, it's more likely going to have more maintenance issues) and the quality of the tenant that's in place.

Also - " Smile , Keep Eye Contact, (no sun glasses), keep your hands and arms open, turn a quarter or half turn so your back is to the front door as it opens, (Smile and stretch your arms out open in your car just before you knock), stay positive, always be closing for appointment, set appointment for future date, get phone # and cell #, bring paperwork to appointment, ask questions as to what is the most important issue with selling this home, craft your pitch around this answer, close deal, repeat process for next deal "Door Knocking in a nut shell ...You will strike out say 9 out 10 times, so what?! 

I just hate to be one that sits back and does nothing like many others that I know which go on to social media boards and vent about the issues. 

I know it's all a mindset issue, and buying and managing a 100-unit property isn't really all that much more work than a 20-unit property, but I guess my mindset hasn't expanded enough to feel confident in doing it.