If it’s value drops 20%, you don’t get to sleep peacefully knowing you rent payments still come on the first of every month.

I believe it was in Podcast #283 or Podcast #288 that they talk about how sometimes it’s best to just offer cash for keys in order to get the tenants to leave the premises on a peaceful basis.

Check for financial assistance at school.Dave ramsey's financial peace university may also help.

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?

About half of my portfolio is paid off, so I get the simplicity and peace of mind of free and clears.I didn't pay down aggressively until about 36 units, and then only higher risk and higher rate ones as deal flow dried up anyway. 

Well, I'm not advising that someone is definitely up to no good, but if they haven't provided you with any type of comfort, peace of mind, and trust that you need just shop around as much as you can.  

This helps me keep track of things and gives me peace of mind to know that I have money set aside for costs as they come up.I maintain the below account structure in my personal banking for the rentals I have in my personal name and also for the accounts of my LLC.  

That is almost comical-there is no peace anywhere when you are a landlord I guess.

I got them for the peace of mind, but honestly, I'm finding that when I do my own work on finding referrals through forums and referral sites, I'm better off.

It didn't enjoy putting the documentation together, but quite honestly, I had more peace of mind knowing these firms were being meticulous about this.