I don't know payroll costs in Chicago, but down here you could pay another $1000-1500 a month for a full time maintenance guy dedicated to your property.

We will both be pouring in sweat equity into the properties and dedicating 100% of our available time into achieving the larger goal quickly. 

However, the challenge I am having is that most of these resources seem to be dedicated to the US market only.

One this is for sure, I am dedicated to this, but I also want to be realistic.

You also have a lot of dedication to take the RE exam 5 times and continue on pursuing this idea!

Given what you've just achieved, and assuming you will again have the dedication to pay down the debt, I suggest the following: get the HELOC; fund the flip; continue to pay down your debt (now the HELOC) with whatever funds you were using to pay down your primary mortgage; set aside/invest the proceeds of the flip for your first rental house; take out the HELOC again; rinse and repeat....    

If I run the job myself, meaning I will act as foreman and just hire skilled workers, then my time is dedicated on that job, but if I hire 3 foremen, I could step to a higher level and make less but volume.

I'm a full time Firefighter/EMT, husband, father of two very active and amazing children, and a dedicated family man.

This seems to be the best fit for my family since at this point we do not have the time to dedicate to developing a market and team ourselves.

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