One year he resolved to "do better about keeping up" - apparently feeling bad that our entire message history was him texting me a month before the convention asking if he could stay with me, and me saying that he could. True to his word, ever after that, he has periodically texted me every few months just to make idle conversation. He even stopped going to the convention but still keeps messaging me periodically - which I appreciate because it shows he didn't view me only as a hotel replacement.
Still, I prefer our old arrangement. Frankly, I don't need to know how he is doing every few months and I find it a bit awkward to make small talk any way. As I just have one friend that does this it's not so bad, but if I had more friends who wanted to just regularly "check in" like this, I'd have to start blocking people, ending friendships, or developing an automated routine to tell the curious that I'm doing well and to ask about their family and our mutual friends, etc.