In both cases, I added mine later for logistical reasons - one house a neighbor on another street was using it as a cut-through and pushing a shopping cart full of cans and bottles all hours of the day.

Now, logistically, something is wrong.  

Then look at our city profile to figure out the pain in the butt factor of the city or town or village and the other logistical things that could happen.

Logistics aside, I've found it tends to be a sign of some financial chaos in their lives.  

They underestimate the risks in doing so, both because of the logistics of the distance, but also because they misprice the risk in the market and asset they are buying. 

I'm half tempted to try managing it myself for a year but we live two hours away so the logistics of tenant turnover are a concern. 

Let me preface this by saying I am no expert on construction, so I won't be able to give you nearly the same logistical info that the people above have given.

We are looking for a good reputable company can handle all those logistics like maintenance, managing the renters which give us LEAST trouble and a piece of mind.

The custodian will handle the logistics of the roll-over.

From your perspective it's a logistical pain and (to the point of others) what if he doesn't come up with the annual commitment?