With my union hat on, of course you shouldn't. Teachers are overworked to hell at the start of their careers. One of our newly qualified maths teachers has been consistently working 11-, 12-hour days since term started. They're going to burn out.
Don't enter grades outside of school hours. Don't contact students outside of school hours. Set up an auto-respond out-of-office reply from the second school shuts its doors to the minute you're back in the building.
Yes I've broken those rules myself, but that's the exception (coursework project over a holiday period, I'll occasionally check my email to respond to questions, but that's questions about the work, not about data entry). Normally my students know when I'm available and when I enter their damn grades. Have a kind chat with this numbnuts at the end of a class, tell him what the fuck's what.
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