I'm frequently guilty of putting up with good enough because I've worked with someone for a while.
My rationalization is always "better the devil you know." I've worked with this person in the past, and they've gotten the job done despite their petulance, poor communication, selfishness, body odor, or what have you. They'll get it done this time, too, even if I'm going to have a rotten day because of them. Plus, let's be honest, I don't like letting anyone down or hurting their feelings.
There's something to be said for loyalty. But once you have the nagging feeling that something isn't right, that the process could and should be much smoother—it's time to find someone new.
As soon as you wonder if it's time to move on, it is because the annoyance wasn't a one-time thing. You've now been nagged repeatedly.
In my experience, the problems never go away. Sometimes, maybe, it's just a clash of styles or personalities, not some awful malfeasance. But that clash isn't going to disappear, and trying to address it often makes it worse.
Find someone new to work with. As soon as possible.
Don't do one last job together. Rip off the bandaid now.
If you don't find someone else, replacing them will only be more painful in the future. And while you continue to work together, you'll not only resent the other person for all the old familiar reasons, but you'll resent yourself for accepting the problems.
I just found someone new (for an operation I handle at Tortuga) after dealing with a nagging devil-I-know for years. The process and outcome of the first job with the new person was much better than what I had been putting up with.
I'm writing this as a reminder to myself as much as advice to anyone else: Next time you're about to excuse working with someone as "better the devil you know," get rid of the devil.
P.S. I should note that Fred is much better at this than me, and, like in most things, a good example for me. He's great at getting us at Tortuga to move on from contractors who aren't doing what they said they would.
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