Hauling a boat as a seasonal thing is common up North but not here so in/out can be a function of where you live.Which, to add to your question, if you don’t mind sir……Do most of you do this while in or out of the water? And what do you use to keep the parts from going everywhere while the service is being done?
Might also be a function of which winch. It would be a disaster if I tried working on my mast mounted winch in situ. And the cabin top winches are in an awkward place to be comfortable working on them so we remove them but the cockpit ones are easily serviced while sitting on the cockpit seat.
From the comments, it appears the consensus is every 2-3 years.
If anyone is curious what the manufacturer recommendation is, I spoke to Harken today and they said every 1-2 years.