He's got a bit of a rough past, basically raised himself from a very young age, served some time in prison, not sure if he's finished high-school, etc.

Just to clarify, my understanding is that I can simply serve them notice to vacate in 60 days (since they've been there for more than one year - and are now effectively month to month) without reason.

I know a lot of realtors like to focus solely on selling and aren't interesting in managing properties themselves.Do realtors refer clients to property managers?

I mean I actually enjoy reading through multiple leases and deciphering advantages and disadvantages it may have for my client!

My current broker who is also a property manager has specifically asked me to "try" to not bring him clients with multi's to manage. 

@Scott Schober one of my clients just bought one in that situation.

Reach out to CPA who works with clients remotely - You may want to reach out to a CPA that works with clients remotely.

They were negligent in dealing with this.If for some reason the tenant cannot come up with any money, serve them a notice to vacate and then follow through with eviction if necessary.

If you dont want to prospect for clients hours every day...this business isnt for you. 

As with most approaches to reeling in clients or properties there is no “best” way (IMO).