The 1st floor commercial tenant alerted me that water from the ceiling leaked all over their computer/printer/desk/chairs. 

A single member LLC the LLC has only 90 days to decide and notify the IRS if it it wants to file income tax returns as a corporation on form 1120  or as a sole proprietorship which flows through to your personal tax return on schedule C.A dual member LLC has no choice.If it were me I would incorporate the company and make it the general partner of a Partnership or Family Limited Partnership.

They think owning a property is a arm chair investment.

We send 1099s to all un-incorporated vendors who we paid more $600 in a single calendar year.

My goal is to incorporate the BRRRR method and use whatever money I can get from refinancing to purchase another investment property on Oahu.

I find some courthouses look at me like I'm a criminal trying to do some dirty work and waste their time while other smaller places ask me if my chair is comfy enough.  

This particular brokerage only operates in a few midwest states, so unfortunately I cannot incorporate all of my properties.

Do I need to incorporate to flip?

I one knows if they were contractor or what.If everything can be permitted it would become a 2300sq ft 4bd/2bth.Now, I am a man that is use to stress and responsibility working management in corporate retail for years.  

If she indicated she was willing to do that, incorporate those terms right into the lease addendum.She still may just say no to the security deposit, but you have really not lost anything by asking.