D&D 5E Voluntarily taking lower Initiative?

[Greenstone.Walker]

At which point I move Bob's initiative card to the new point in the turn order, and we move on.

What happens when Bob is last in the round and still says "Ummm"?

It seems like it would be better to deal with the underlying issue and make the problem go away for ever, rather than make it go away until the next round, hoping that the combat doesn't go on for longer that (number of players +1) rounds.

Perhaps, "Bob, this is not a combat simulator, it's a board game. You've got four or five choices, none of which are horribly subobtimal, so pick one and go for it!"

 

[delericho]

What happens when Bob is last in the round and still says "Ummm"?

It's a cyclic initiative system. Last in one round is the same as being first in the next.

It seems like it would be better to deal with the underlying issue...

Normally, I'd agree. But it doesn't work in every case, and in particular it doesn't work in this case.