Only need to calibrate once unless you move to a different location 100 miles or more away. Other times to recalibrate are after firmware update or if you are having some toilet bowling (circling when it should be hovering in one spot.)
First time and after any resets of St 16 or firmware updates. Do it a couple times to learn it. It can't hurt. Let H settle after that first time once initialized and gather all satellites even after GPS lock. If you go to another location (they say 100 miles but here in Az I have no problem between Phoenix and Tucson when calibrated in Tucson) you should recalibrate.
Good idea. Try not to hurry and learn one aspect at a time. Keep it within sight during all this in order to know what it's doing rather than hope it's doing it.