I am in the process of outgrowing my current market and would like to to move to bigger MF opportunities, in larger markets. 

As @Cat R. said, it can open up a lot of opportunities for unnecessary issues. 

Working as a property manager I have developed a passion to be my own boss. I am ready to take the first step in what I hope will be to build a property management company. I am interested in purchasing to either rent...

Some of the local municipalities here will contact a taxpayer with a letter essentially stating you filed a Schedule C, but you don't have a business license - explain this to us.I don't know that California does the same, but the opportunity is there for them.Best of Luck with Your Real Estate Investments!

The venture-specific LLC will offer more liability protections, and you will have the opportunity to craft an Operating Agreement that puts a "clock" on the details of your deal.

Also, what are the fiscal pros and cons of wholesaling?

If your ratio is bad, you will not easily get a loan if and when a good buying opportunity comes along. 

While I am currently house hacking with this property I am always looking forward to find the next best opportunity.

I'm ready to purchase the next one or two multifamily investments in suburban Chicago, and see this as an opportunity to start building those deal-finding relationships for the long term. 

Seems like a really good opportunity if truly in a B to B+ area.