Yuck. If interacting with me is such a chore that someone has to automate it, I'd rather not hear from them. People don't want to be your duties. They want to be your pleasures. This changes messages from "I felt like talking to you" to "my scheduled trigger fired; please start a conversation so I can check you off my checklist." If I found out someone were using this to communicate with me, I'd frankly cut them out…
Am I a bad friend because I do that? If not, why is it so different than texting someone because you haven't interacted with them for a while? Would it be better if instead of automatically texting them, it would "remind you" to text them and give you a text suggestion?