I would get younger trainees in the next few seasons so you can train them as backup trainees if you want to, but they don't become liabilities with how slowly they train when they get older. I don't think any of your guys will actually hit their caps, so just whenever you feel like rotating down to a younger trainee or two.
Also as for the offsite! YAAAAAS you have joined the cool club. I approved you, so feel free to introduce yourself on there!
Murray/Harris/MPJ/Grant/Jokic - 2020 NBA Champs