Sign him up for the grade he WILL BE in the fall during the season.
While specific dates will vary from year to year LYF and the UYFC (Utah Youth Football Conference) try to mirror the Utah High School football season as much as possible. Try outs (if applicable) will begin the week following the 24th of July Holiday. Practices can begin after tryouts, often the first week of August. The first games usually start the second week of August. The Jamboree will be the weekend before the first games.
Yes, games are typically scheduled and played on Labor Day Weekend.
No. Typically games are not scheduled or played over UEA weekend [aka Fall Break]
Grades 1-3 selections are based as close to school boundaries as possible. However, the coaches are given some leeway. Grades 4-8 selection is made specifically through coach evaluation of his team needs and player skills. 9th grade is one team.