Evaluate Property ConditionOlder Chicago buildings often have charm—but may come with hidden costs.

It would cost a lot to get the planning approval and do a complete renovation of the 2 units.Can anyone suggest what would be my options at this point?

All those things, and more, need to be ironed out.Question 2From a tax perspective, if you put a dollar in a business and when you sell you get a dollar back, that is a $0 profit, so from that perspective there is no tax. 

If you don’t have a clear understanding of your cash flow, operating costs, and future expenses, you could be setting yourself up for financial stress down the road.The Power of Financial ClarityYou can’t make smart decisions without knowing the full picture of your finances.

Of course don't go there just looking for business, you go because you believe in whatever the group is doing. 

.- Expected renovation costs $1MM.

So if I do a good analysis of the property (including all the costs) and the property generates monthly CF with a DSCR above 1.1, I would be removing a big risk because the numbers add up.

If you try to do it all yourself, the risk is much greater because there are many more opportunities to make a bad decision that can be very costly.  

My money market funds are dedicated to go towards a down payment, closing costs, etc.

Hard money typically refers to a company that has it's own underwriting guidelines, rates (9% - 15%), costs, draw process ect.