once a year-ish. Usually about the time I think it might get caught around some rain. Texas weather is pretty sparatic at best though.
Didn't do any oil bath on mine. I assume it's supposed to soften it for break-in (that's what most suggest). I suggest lots of short rides if it's uncomfortable out of the box. Going at it for 100 miles on something that is still uncomfortable isn't going to help.
Mine didn't feel "bad" out of the box, but not great. It was SLIPPERY with lycra... which got better once it had sit bone grooves worn in. That was the uncomfortable/annoying break-in IMO.