Ask once. As much as possible, calculate the total cost of uniforms, travel, equipment, and whatever other essential expenses you know each player will incur, and then present this number to the parents, ideally before the season begins.
We know this is hard to do; schedules change, and tournaments you plan on registering for might not be as organized as you are, releasing dates and costs into the season. But if you can ask once, instead of begging for money throughout the year, parents will be better able to budget for your team's costs without feeling like they're being nickeled and dimed.
Set deadlines. In order to underwrite the team's success, you need money by a certain date. Consider charging a late fee if a family's funds aren't turned in by then. While coaches have administrative responsibilities, you shouldn't have to be chasing parents down for money, particularly when they know that joining a travel team comes with a certain financial commitment.
Make Payment Simple
Require electronic dues. Before you balk at this idea («but my parents will never go for it!»), think about two things: first, many parents like the choice of paying by credit card; and second, you'll eliminate the possibility of any lost checks! We promise that your record keeping time will be cut in half because services like Pay It Square take the hassle out of collecting with templates for sports teams and features that track who paid and who hasn't.