I'm a real estate broker in Chicago and I'm not saying you need another agent because I want you to choose me, but before purchasing you should interview other brokers to find one that best fits your goals, needs, and wants.

Hire a qualified eviction lawyer.Your tennats goal from this point forward will be to live free for as long as possible, to do that he will use the courts to his advantage and file extensions and appeales aftr every ruling.Hire a lawyer immediately and make sure he has experience dealing with professional tennats. 

I'm going to practice analyzing deals based on the 70% rule for flippers.TLDR, my goals.1.

Cash flow is my goal.

Is my profit margin goals to low/high2. should i buy and hold every other house or two to start building cash flow now or just keep flipping untill i can roll on a 'big' complex or something3. 

My goal is to convert all of my units to government program funded, so this might not make sense since it seems as though most government programs require that the landlord pay all utilities anyway.3.

The goal is to buy 7 units a year for the next 5 years.

So it really depends on what your goal is.

If you or your spouse qualify as a 'real estate professional' and meet material participation regarding the property, the tax losses become non-passive and can offset other taxable income.Good convo to have with your tax CPA/EA who can consider your facts, circumstances, and goals.

The key is to identify your goals and the strategy that will align with them.