@johnsubira Your gut feeling of $50 per person who works closely with your kids sounds like a totally good number to me!! And if you do $20-30 for those who work less with your kids, i doubt anyone would take offense.
Example of what we do, in case it helps others gauge their holiday contributions:
At our former daycare, we pooled money from parents to split across all ten full time staff members (some parents did their own gifts). The director and daycare owner both floated among classrooms but got the same as everyone else (but they also do a lot of work so that felt totally fair). Parents gave anywhere from $50 to $400-500 — I usually gave $300-400 total depending on the bonuses we got from work.
This year we are in a larger school with pre-k through 9th grade, and there’s also a pool to divide amongst all staff. Gifts here have also ranged from $50-500. I donated $250 to the pool and we will probably also gift $20 each to the teachers in my son’s classroom. This way I know all staff will get something, but can do a more personalized card for the teachers that work closely with my son.
This happens to be what we can afford & is not going to be the same for everyone! We make pretty decent salaries but are not wealthy, and budget for teacher gifts of this size each year; so it really depends on your own budget.