If a player is on the same team for 2 seasons, do I need to have separate records for each season?

No, the start and end date can span one day or multiple years. In the screen below, the Player was on JV for the 2003 season and joined the Varsity for the playoffs at the end of the year(5/20/2003). He remained on the Varsity until he graduated in 2006. This player also has his College team among the records (his dad used LAXSoft for both his High School and College careers). A player could move back and forth between teams as many times as needed. A player is “active” on a team until you change his status.

Player Team Assignment
Player Team Assignment