I started out on the same path that most rental property investors do.  I bought a single family rental while working a full-time job, kept acquiring more rentals over the years while self managing, until I hit about 20 units.  At that point, I decided I wanted to get bigger, and had to swallow the bitter pill of giving up some of my hard earned cashflow to a 3rd party property management company so that I could keep my sanity, my job and my family life while continuing to grow the business.  

I will soon have over 60 units, the majority of them now multifamily. While my life has gotten much easier since hiring a PM, I keep thinking about eventually bringing it back in house and hiring a property manager to work directly for me so that our financial incentives are better aligned and costs can be reduced.  I am at that awkward size where I am not really big enough to hire full-time staff, but too big to handle on my own and do a good job at it.

I would like to hear from others that have been through this transition.  At what point (number of units and/or revenue and/or expense ratio) did you make the decision to hire staff, and is the person full time?  Salaried/hourly?  Benefits?  How do you provide incentives for performance?  What skills and experience did you require?  Do you have the person handle the front end activities (advertising the properties, showings, leasing, customer service, dispatching) as well as back office (collections, bookkeeping, technology/CRM)?  

Lots of questions, obiviously, so I appreciate any veteran feedback.