For Schedule H, Line 9. I paid one babysitter more than $1000 in one quarter. We also used a drop in day care where I did not pay over 300. what do I check?

Check Yes.  The question refers to the total you paid out in any one quarter.

Thanks, that is what I though but the bolded "All" made me question

I checked "Yes" for this case and Turbo Tax keeps giving me an error saying yes should be blank.  Good luck with yours!