It sounds as if you are pushing to justify a decision when you already know in your gut that he's not the right fit. 

If often more that they are abandanoning the property to the government because there is some type of constraint, i.e. there is a street light oddly placed in the middle front part of the parcel, there is a creek or wash (which means environmental permits would be needed), there is lack of true legal access, zoning problems, etc. 

I do feel I'm stringing myself out a bit with adding this deal to my current workload, but also feel I can adapt and conquer and maybe push myself into multi fam.           

Don't look for the agents pushing their card into everyone's hands, look for investors who also work as agents.

That being said I don’t allow any portable dishwashers or portable washing machines because we have experienced too much damage from operator error.

I have actual work to do and don't need 30 days of this.He never paid me the expense deposit in my management agreement and I never pushed on it because I'm always holding enough of his rent at any given time for it not to matter.

decent lawyer will shred him in depot.. was he lying then or is he lying now.regardless I can see 7 figures going out for legal defense and or more if he gets criminally charged. and he better have paid his tax's  LOL that's how they got Capone as we all know. 

You'll need the tenant to sign it as well.That said, if you want to retain the tenant there are some things you should consider before pushing the rent way up in one go. 

I asked him in what ways was he educating himself in real estate.  

car wash ?