This is where a checkpoint differs from snapshots and backups. They serve a very narrow purpose.
I try to explain it in this thread.
You really don’t want to sit on a checkpoint for more than a few days or so. Otherwise, it loses its usefulness.
On the other hand, you don’t want to neglect creating one temporarily, so that you have a “recent” safety net in case things go sour shortly after.
Think of it like this. Let’s say you created a checkpoint back in July. That’s about 6 months ago. How useful is this safety net from 6 months ago?
If you rewind your pool back to July, you will lose everything after July.
If you had created a checkpoint on November 17, then you’d only be rewinding back for 1 day. A safety net from 1 day ago is much preferable to one from 6 months ago.
The reason (theoretically) why “automating” this to follow closely behind you by about a few days, is to provide an “always recent” safety net at all times, for those of us who are prone to neglecting or forgetting to use this feature when it matters the most.