My comfort level had been established by setting our rough estimate at no more then 18K into this flip.

I would talk to him (if you're comfortable) and let him know the behavior is unacceptable, that you are concerned he may end up in jail and unable to pay rent or stay, and it would be in everyone's best interest for him to leave now rather than be forced out.

The question becomes, what level of umbrella coverage (Policies are sold in $1,000,000 increments) are you comfortable with and whether or not the added protection of the LLC is worth the cost at that point. 

I think you are on the right path but only you would know what you would be comfortable with – investing wise. 

Ultimately the landlord is going to come after you for any damages and rent and that is not a responsibility I would feel comfortable taking. 

And if you are already in contract - well now you get to figure out your comfort really fast. :)

Some of my goals are: -Retire Early (30-35 years old)-Live very comfortably or better with the ability to travel when and to where I want-Have more time for friends and family -Build generational wealth for my future familyI know that this is a lot of information and can most likely have a post for each section I covered but I wanted you guys to get a little picture of my life, where I stand, and where I want to be/when I want to be there.

That is exactly the strategy I've followed and built our business on is investing in areas that maximize cash flow, ROI & Appreciation. 

@Neil Martin some of this will depend on your own personal levels of comfort.

It's most definitely possible if you're looking to maximize your cash flow.