Get out there and take risks, have balls to ask for money or information, present yourself well, and you'll be all set.

I don't know how much of a difference cook county is than Dupage when it comes to utilities but I would assume its in the same ball park.

It seems like if it's a sellers market, low supply and high demand, the ball is really in their field (or sand box).

@Phillip Dwyer may be able to help but no realtor I know has time to submit a bunch of low ball offers.  

However, we are driven to get the ball rolling with our investment/flipping team!  

If so, I would send the HOA a letter stating where they dropped the ball, and demand the full amount refunded or you'll exercise your right to go to small claims court and get double your deposit back.Hope this works out for you!

No one has a crystal ball right?

That would allow you to keep the ball rolling.

But I figure best to get the ball rolling by serving an official notice when having a conversation.

The cash flow would either serve to pay of our bad debt faster or put back into the properties (or get the ball rolling on another property, given we can find a lender)Someone mentioned that wholesaling is a full time job, but several of the guests on the BiggerPockets podcasts have done wholesaling part time to start.