It seems to me the biggest factors prompting a desire for property management are: those that aren't handy, number of units, age (I imagine I will have a PM when I'm older and tired and can't crawl through the attic anymore :), out of state investors, and those who own properties in less nice areas.  

Biggest piece of advice, make sure the HML you choose is a DIRECT LENDER, this makes a big difference in the investment world.

One of the biggest frustrations with internal business partners was  push back on stating expectations and requirements up front on projects, and then hearing that "You never told me that" when things went sideways.  

The biggest payoff is the stepped up basis at death, its capital gains tax free to the heirs, which is another incentive to sell.He tells us he finds his buyers by cold calling, calling owners that owned properties for about 30 or so years.

The biggest thing you need to decide is "What do you need it to do for you?"  

Vacancy is your biggest expense.

The biggest challenge was working with contractors long distance via before and after pictures.

My biggest concern is how to secure his belongings and how to legally handle any family that wants to get his stuff from the apartment.  

The biggest factor in my decision to do some new construction is that in my area older homes from the 70s and 80s usually sell at a price level that I could construct a new modern home with half the energy cost and quality materials and the style of a much more expensive home and still make a healthy profit margin.  

Now the average property manager gets paid less than that per month to manage one of the biggest financial investments in your life.