I spend less than an hour a month dealing with them. 

What do you mean you are paying $400 additional dollars more than what you are paying now?

I have about $100k in capital reserves and can leverage the 2 properties for additional capital, as needed.

Spend your time and money learning how to avoid that kind of situation rather than learning from on the job training.

Some carriers won't allow insured to be a trust, so in that case do it in your company name with trust as additional insured.

I’m unable to invest in areas familiar to me as I’m priced out of suburban NJ where I was born and raised.I’m looking to spend $150-$180K on a condo and will need to research viable areas.

Additionally, some states hold Escrow and Title services differently. 

Quote from @Conte Cuttino: Makes sense @Andrew Freed so say if we I can make it additional legal space, do you think the 107K left in the property for the return is worth it or should I sale and move on? 

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Additionally, regarding the legal structure, an LLC seems to be the most suitable option for our situation.