workflow: condition never triggers on datetime field = 'now'

I am sorry but I am not sure I understand what yo are trying to say. Could you be more clear please?

Maybe you are worried that, once the condition is met, then the action will be executed every other time the condition is met (which means always).

To be 100% sure you can add a custom boolean field which is set to TRUE when the condition is met so, if in your condition you also check for that field you will be fine.
In any case, you shouldn’t have the problem.