Purchase price: $565,000 Cash invested: $125,000 Listed Price: $585K (originally $585K, 30 days on market).

There is a guy near me with 6 small houses he rents , he has a waiting list .

Are their listings detailed with good-quality photos?

I had waiting lists of tenants for the first and only time in my career. 

It's been listed on MLS for about 3 mo almost with no traction.

I'm a listing and buyer agent.

The current owner listed last years income as $51,000, but currently has rents at (for the five separate units): $650, $750, $800, $825, $1125 (the math doesn't totally add up so maybe he changed a rent payment at some point). 

REI Game Changers is a beginner program that relies on cheap spray and pray list marketing.

Ask the listing agent for a list of known issues.

I highly suggest getting to some local meetup groups...here is BPs list:  https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a full list of the chicago meetups that I can share with you too if that'd be helpful.