All income I make, I can have various types of expenses deducted.  

Cleaning is expensive because they clean or remove every square inch that could have come in contact with meth smokeSo the risk from tenants is no less than the risk from selling it to a new buyer.  

hard money is short term money... and expensive.. not intended for periods of over a year .. interest and points will kill any cash flow investment. 

However, for the amount you have, the expenses and paperwork, I wouldn't suggest going down this path. 

You live in one unit and let your tenants pay the mortgage and other property expenses.

You build wealth by increasing income and minimizing expenses.

I love the East Ave/Park Ave area and know it well because I lived there for 4 years, but I think it might be a little too expensive at this point. 19th Ward and South Wedge seem more in our target range.

I am assuming insurance, taxes and some local fees would be applicable as part of the expenses. 

It's a little farther north/west, however, the houses are newer and less expensive and you can still get great schools. 

I was going to look at the renovations not as an expense, but as value creation, as future equity that I could tap into.