It's definitely NOT dead, but, cash flowing or breaking even is significantly more difficult. 

You can sell the property and hopefully break even, chalk this up as an educational experience, and try again.Next time, look for property with more wiggle room.

My biggest piece of advice is to connect with local chicago real estate investors in person...highly suggest checking out the christmas party on 12/12:  https://www.biggerpockets.com/forums/521/topics/1218823-chic...

J Scott breaks down all the fixed costs on closing a wholesale/flip deal.

you'd have to break it down to some like for like comparisons to come up with a more "general caprate for a specific asset class" or something like that.  

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For 7 months straight I was -$300 to -$700 a month because of repairs called in by the tenant (tenant   wasn't breaking things as confirmed with Property Manager).A 100 year old renovated house is going to have problems.  

I’m looking for a structure that would at least allow me to break even, or create capital through something like the BRRRR method to use for future deals.

If you rent the basement room to someone or market the house as a whole counting the basement as a bedroom and a fire breaks out and someone dies or is injured in the basement without an appropriate egress from the room you could be liable for all of that.   

We had the plumbing break down and had to install new PVC plumbing Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?