One piece of advice. I would not order any parts until you are ready to do your 1st top end. At that point, I'd do both piston, ring(s) and the wrist pin needle bearing. Pick a brand, OEM, Wiseco, etc., and stick with it. I don't believe you can use rings from different brands. Example you cannot use an OEM ring on a Wiseco piston. After that I'd follow the process you posted. As for when it time... that is where the compression tester in invaluable. After you do a complete top end, use the compression tester to set a base line. From time to time, recheck the compression against the baseline. When it starts to decline too much, its time to freshen up the top end.
My son used to ride a 99 YZ125. We purchased it with a fresh top end. He rode it for 2 years, (trail riding mostly), I sold to a friend of mine. He has ridden it for 3 years... In all that time its still running the piston and rings that was put when I bought it. I have told my buddy, that I am going to steal the bike and tear it down and force him to redo the top end... It been due for quite a while but she just keep on running. These bikes really can take a lot of abuse. With some basic maintenance they just keep running.