I find that finding reliable and quality service vendors is a numbers game just like getting good leads.  

If his income dries up, you still have 30 days to get rid of him and another month for cleaning/repairs.

A property manager will cost 10% of $2,000 monthly rent or $2,400 a year, possibly less.Do yourself a favor and find a good, quality PM to handle this for you.

Been a land lord since 2005 and only had one security deposit disputed informally (i.e. someone said it wasn't fair) over a carpet cleaning fee. 

Are their listings detailed with good quality photos?

To defend something like this will cost you $25k+ but they will settle out of court for a Quarter pounder with cheese a large fry, small strawberry shake and $5k and wipe the note clean.

We now have two extended stay fully furnished rentals, decked out with the finest furnishings and twice a month cleaning services. 

Listsource is a great site for generating quality leads.

In the "MOVE OUT AND CLEANING INSTRUCTIONS" when it says "If Tenant intends to move out, Tenant must give Landlord ___ days advance..." 

@Brendan Connolly only you can make the determination whether or not you sell your current property and buy a higher quality asset or whether you should pay off your current property or look to borrow and increase your holdings.