Let's just throw this one out there. Seems like a no-brainer, yet inexplicably the previous park director never moved to Naperville...
There are many reasons why public officials should live in the community where they work: they get to know people better, they pay taxes like everyone else, it's a symbolic goodwill gesture. Heck, it even gets politicized in places like Chicago where rank and file teachers and firefighters have to live in the city.
Not every town can afford residency requirements. It would be tough for a Naperville police officer to find a decent place to live in town, on his salary. But what about for park district executive directors?This is a job that pays in the $150,000 range, so surely this person could afford to live here.
Should the Naperville Park District require its director to live in town?

Absolutely they must live in town. Call it a 'vested interest'.
It's also called "eating your own dogfood".
Make the directors and the top policymakers live in town. The average civil servant's salary can't buy a house in Naperville.
This a silly, but emotional concept. People work in many enterprises and live in many places without impacting the effectiveness or quality of the effort they apply in their profession.
Let's make a rule, for example, that all Edward Hospital doctors must live within the Edward Hospital service area and only use Edward Hospital for delivery services. That will make them provide their best service to patients at Edward Hospital. All teachers must live within their employment school district and msut have children or grandchildren attending schools in the same school district so they will teach better. If you work for Miller, you better drink Miller brand beers (even if you don't drink alchohol) because otherwise you won't have a vested interest in making or delivering a good product. If you made dog food for a living, would you live on a diet of dog food? This is emotional hogwash.
There are much better ways to evaluate and receive good performance from employees and leaders. Residency requirements simply reduce the pool of talented people from which you can choose. Naperville has only an approximate 10 mile radius; relocation expenses for a job are only detuctable if the move is more than 50 miles. Should the park district start paying for unnecessary moves when an individual already lives in the Chicagoland area? And most couples are dual income families. Who wins out if both spouses are in a profession that has a residency requirement in two different locations. Do they have to maintain two seperate homes?
This is just stupid and doesn't provide the desired result. If you don't think the leader is aligned with the interests of the enterprise get a new leader.
Yes, they should live in town!