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I always assumed that McGonagall sent the letters, since they were signed by her. (Yours sincerely, Minerva McGonagall, Deputy Headmistress)
I have a mental image of her spamming Gemino! on stacks of letters and taking them up to the owlery.
And probably thinking like “That kid is not even in school yet and already causing hassle for me. Will be good 7 years with him in my house”
Well, she didn’t know for sure that he would be in Gryffindor at that point, but she did know he was James’ son.
He really did enjoy messing with them as we saw when he visited.