I think you're on the right track, here. If you have that much of a difference in talent, I'd do the "has played/never have played" split, for sure. Last thing you want is to be slammed in a small gym and someone get hurt. I've been there, not fun. Plus, you could then adjust your drills/skills appropriately for the majority of the groups. Or if your numbers are still really uneven, could you look at splitting up 9/10th graders and 11/12th graders?
I'd also add, at least, one more day. I'll probably have around 24-28 for "tryouts". We'll have V/JV, so obviously not cutting anyone, but we have a 4 day tryout with individual meetings on the 5th. Do a couple skills a day, with each group, then maybe have all who want to pitch come in together, if you have enough to catch, or throw into nets...whatever you need to do.
Wish you the best!
Thanks!
Our talent is basically our handful of best players, then a big group of girls who have played with us 1-2 years who know what they're doing but are still very much developing fundamental skills still, and then the group of girls who I have to tell which hand the glove goes on (I literally did this at Open Field yesterday). I really think dividing into multiple sessions is going to be the smart play here, both for safety and evaluation reasons.
Tell me about your individual meetings. Do you meet with everybody? Is it just to go over expectations, roles, etc? I did this last year with a few girls who I planned to have float between JV and Varsity just so they understood the plan, but I've considered doing this type of meeting with everybody.