With the two persons method it is really simple: one pumping the pedal and the other cracking open the valve to get the oil out. The key is to not lift the foot from the pedal until the valve is closed and to keep topping up the reservoir, plenty of good vids on YT. Also important to use a good quality tube, I have the simplest kit from BGS and works great. I have now got their tube with non return valve so as to be able to do everything by myself. If you accidentally get some air into the caliper, just bleed some more
Absolutely not, I have done all of 2025 (20k+ km and 5-6 track days) and when I went to bleed the system there were barely any bubbles (but the oil was definitely a tiny bit darker than the fresh one, maybe because of some water starting to get mixed in?). This year I am trying to do it more often to chase the cause of the pedal going softish after consecutive push laps, but I’m getting convinced it is not the fluid or at least not an all out boiling issue (maybe air trapped in the ABS circuit or just an effect of having the whole caliper pretty damn hot and losing some stiffness)