If you're in a hot area you stand a good chance of getting buyers to compete for it and driving the price up.

I would love to meet you and your team when i have a chance to travel to Chicago!

Making a few thousand then cost him the chance of making a whole lot more later on.  

And what approaches should I use to increase my chances at connecting with investors/mentors?

Chances are you won't have a lot of people in your corner supporting your idea so be strategic in who you ask for advice.So my "lifestyle design" in a nutshell- I started my own company that I work on whenever I want.

It's disheartening to think, there's a pretty good chance you know, are friends with or even have as family an offender...They are all over. 

So look for neglected maintenance issues.Since this deal will likely require a major investment of your time, keep in mind that there is a strong chance it won't close (It's a CL ad, it is your first deal, property is probably terribly mismanaged, you may find some major issues that will kill the deal, etc).  

Obviously a bad idea, but statistically some people will get away with it, then come on the forums and say exactly what you mention, perpetuating the cycle.However as you start acquiring more properties, which I'm assuming is most people's goal on here - to have a substantial amount of passive income - the more individual properties you have, the more chance of at least one big ticket item each year.

It gives me a chance to see the area.

I would have enough for a 20% down payment in several months, but I'm afraid I would lose the chance if I wait too long.