Just an observation - as the kids get older the showcase type teams will be looking for commitments from January through December. Because of the lead time required to enter the fall tournaments you really need to have your roster, and funds, in place before the normal August tryout time.
You bring up a good point with the time needed to get a team together and to get he funds needed for not only fall events but, for the many "summer events" that require payment by December. We split fees into fall and summer fees so it is not a drain on the families and they can budget accordingly.
As an organization we have been fortunate to maintain the majority of our players over our seasons with only needing a few from season to season with the exception of this years 18U since we had so many graduate last summer (7).
Our saving grace (that many teams do not have) is being part of a larger solid organization where players are more available as they move up in age.
So, I think the tryout philosophies may differ for organizations with multiple teams opposed to the stand alone team. We like the all age group in August and as needed after or as needed.
As far as breaks or schedules... over the past 5 years my 16U-18U teams played a full summer schedule starting in June with one weekend off and ending the first sometimes, the second week of August.
Like most tryouts starting in early August and then starting practice once or twice a week after labor day playing 3-4 showcase tournaments and getting the ladies ready for college visits and camps and fall events including SAT/ACT test prep for those that need it.
We have had good success with college looks in the fall so, I would suggest playing Summer and Fall for sure at 16/18U...
Practice throughout the winter 2X a month Dec, Jan, Feb taking tome off for Thanksgiving Christmas and New Years... Then the ladies start HS workouts in late February and come back together as soon as the HS season ends...
Sounds like a lot. But, the ladies do get time off to visit perspective colleges while staying sharp and have the time to play another sport ...
My DD played Golf in the fall and Bowled in the winter... she was able to attend dances/school functions, band etc... We have others that played BB and Volley Ball.
As far as my vacations or parentdown time... I take my vacations during our summer events... we just head out a few days early or stay back a day or two and check out the cities or local tourist stuff. Some parents do the same while others vacation in August after the season or on the off week in season.
It is important for the family to have their time especially; if there are multiple siblings. Real nice when heading to Tenn, Chicago, FLA or the East coast for tournaments...