If your problem is that you're busy doing things, an email in the morning (probably not the only one you have) is not going to help too much. Contacts will still get delayed in favor of other things. To me, the OP system reads like a system that doesn't help with scheduling, but with triggering the thoughts.
For example, say that a friend tells me they're going through a rough time and I want to spend some time talking to them, but I'm busy and don't have that much time. The system doesn't have a "contact NOW" trigger, for example.
I also find it weird that there's a "three week contact" category. I'd guess that for close contacts, something reminds you of them every once in a while, you probably don't need anything more than "hey what's up" in a message so you can send it whenever, and they probably also contact you frequently. I don't think the system would be helpful in those cases (mainly because the DB and the actual contacts would quickly desync and the reminders would not be on time and appropriate) so I'm left wondering what's happening there.
> Most importantly, I always send the kind of messages I’d like to receive. They’re short, genuine, and (ideally) helpful. I never try to sell anything and there’s no agenda other than to keep in touch.
You might've read that:
> So unless you have a solid system, chances are high that you won’t reach out to people regularly and miss out on a ton of fun and opportunities.
but intentionally miss the fun part and treat "opportunities" only in thebusiness context and do not allow for alternative interpretations like intellectual or personal development.
Unless you are in college and have little to no obligations, it gets hard to stay in touch with all your friends and keep track of what is happening to them. It’s not treating people like assets. He is putting efforts on his side towards keeping connections and to do that he needs tools to help.
What does it change that he uses reminder to think about reaching out? In the end he is still the one doing work towards fostering relationships.