For the most part we have been leaving it in except on windy days when the pin is leaning toward the direction of the putt.
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Call me a sinner or call me a heathen, but we count those putts as good. Not if it glances off the side of the stick as it goes by, not if you bang it so hard that it would have rolled 3 feet past - but if it was on line and had the right speed to drop but got rejected by the pin, that's a made putt in our book.If playing alone, pin in. Saves my bad back some. If playing with others who'll share the work, out. If most want it in or out, I'm fine going with the consensus.
I'd probably prefer pin in all the time if it weren't for our flagsticks. They're too thick and firm at their base and although not frequent, I've had 3 incidents (regular holes, not covid accommodation) where the pin clearly rejected a putt that was certain to drop otherwise. They were highly annoying.