But it's a good idea to keep up with the versions anyway. The upgrade processes isn't really complicated and if you can afford a downtime not really challenging.
In my experience it's typically easier to migrate from version x to x+1, rather than waiting a long time and then migrate from x to x+5 (or similar big jumps).
But regardless of the strategy for major version upgrades (10 -> 11 -> 12) you should at least keep up with the minor updates (10.1 -> 10.12)
I've got pgBackrest set up for backups and pgBouncer for connection pooling set up so it's a case of wondering if there is some benefit to the newer versions for someone using it "casually"
Since it's require quite a bit of reconfig and testing.
EDIT: forgot, pgBouncer also allows you to do hitless restart/upgrade, which is useful at any query volume I suppose ;)
Also the server the DB is on is RAM constrained. And Postgres making a process per connection brings it right down versus using pgBouncer to pool connections.
It seems complicated but it's actually quite simple.
I haven't upgraded but would it actually be worth the effort?