Looks like dollar for dollar a used police bike is a good deal, if you a willing to gamble on the service and maintenance quality.
Service and maintenance on a police bike is the one thing you are NOT gambling on. You need to look at the agency the bike is coming from. If it is an accredited agency (which most that are large enough for a motor unit are) the city is required to maintain their vehicles at regular intervals. In fact most of the Harley police bikes are leased to the city for X amount of time. During this lease all of the services are performed by the dealer. After the lease is over the bike is returned to Harley where it is sold. Therefore all services have been performed by a Harley Tech.
However, just because the services have been performed does not mean the bike will be perfect. You need to look at the type of work that motor officers do. They are mostly responsible for traffic which involves traffic enforcement, wrecks, parades, etc. Imagine the wear on an engine during traffic enforcement on the interstate. Officer sees a speeding car and roars down the interstate to catch it, stops the bike. 10 minutes later same thing start, full throttle, stop. Imagine going from stopped to full throttle and stopped again all day long day after day. Now look at a parade where an officer is riding 5mph. That's alot to ask for an air cooled motor.
On the other hand a police bike is like a blank canvas for customizing. They are great candidates to be turned into really cool machines. They start out less expensive than the rest so you have some extra money to put into it. In the end it's all just a matter of what you like.