Some places use touchscreen keypads for PIN entry exactly for this reason: to allow randomization, e.g. for opening a locked door, or for authorizing a transaction.
I’m sure it depends on the application to some extent. I can type my pin in without looking at all, so I can cover it up while doing it. If I had to hunt and peck, it’d easier for an onlooker to observe my slower motions I think.
But if I used the same machine often enough to produce wear specific to me, this randomization would be really useful.
I use a randomized PIN pad on my phone, and I've gotten quite used to it. I can enter my PIN almost as fast as I could on an unscrambled pad; it's definitely not hunting and pecking.
I’m sure it depends on the application to some extent. I can type my pin in without looking at all, so I can cover it up while doing it. If I had to hunt and peck, it’d easier for an onlooker to observe my slower motions I think.
But if I used the same machine often enough to produce wear specific to me, this randomization would be really useful.