I have a kind of an odd questions for fellow landlords or if anyone is in the insurance side.Last year when Irma hit South Florida, I suffered quite a bit of damages on a number of my rental.A particular one is a multi family building - I had fence damages, tree branch fell on roof, poked a hole through the roof, through the ceiling, debris everywhere inside, outside...so I filed a claim to my windstorm insurance carrier.I was lucky that the apartment the branch went through, was vacant at the time. 

@Youssef Menkhour congrats on securing your first property and negotiating on your second.I agree that landlord expect a negotiation after the inspection (as they know the repairs that are needed) but there are a few that wont budge.

The way i understand it, a short sale would benefit him if he was preforeclosure or considering filing for bankruptcy BUT he is already in both.

Most Hard Money Lenders have a minimum of $50k.Here are two good resources to find lenders:https://www.scotsmanguide.com/Residential/LenderSe...https://privatelenderlink.com/You can bring in a private money lender to provide the $25k secured by 1st Trust Deed.Where is the property located ?

Without bringing up the lease again and aggravate him even more as he wanted to talk to his attorney (according to what he said/presented he is a kid with rich parents with attorney), what some other ways to minimize the situation (ensuring no random security issue / damages on house and car), get my garage and driveway back, and get him to leave peacefully as soon as possible?

And you cannot purchase property from yourself to complete a 1031 exchange.If the LLC files as a partnership and files it's own returns the that LLC is the tax payer for the property and not you the member. 

We made an aggressive offer and secured the land.

I think in might add more job security and bring more people to that location but again, those are not the hi-paying jobs like it would be the case of amazon HQ2. 

I've had many LTR's where after a year I have to repaint the entire home, replace appliances and do other repairs that easily exceed the security deposit. 

. ($500K if you're married and filing jointly.)