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[LudicSavant]

The problem is that this is only realistic if you're playing a MMO (and even then, it's a giant pain in the ass) and not role-playing a character.

Try it out. Set your phone to a fifty-seven second timer. Every time it goes off, spend three seconds resetting it. For eight hours. See how much your productivity suffers. Do it while you're around people who have to put up with it. Insist that you have to keep doing it so that you'll be prepared in case there's a fight. You'd be the most annoying prepper ever.

My perspective on this as a DM:

I wouldn't necessarily assume that a bonus action takes 3 seconds of undivided attention fiddling with your phone. It could be as simple as snapping your fingers.

Also, being ready and on high alert through the entirety of an extended breach and clear scenario (which is basically what a lot of dungeoneering is) would not only be possible, it's... pretty much just what you do if you value your life. If you had to press a button every minute to keep your phaser charged on a dangerous away mission, you'd do it.

As such, I would find it entirely reasonable for a player to maintain shillelagh the entire time they were in the kind of situation where they would be moving about with their weapon drawn and at the ready.