For me, my tragus piercing was the least painful piercing I had, and to this day its my favourite. Way less pain than cartlidge, navel, or a tattoo. And waaay less painful than childbirth. I also found that it healed really quickly and easily as it didn't tend to get caught on my clothes or anything (the way a navel or a nose piercing would).

I am pretty sure that it is okay to get a piercing while breastfeeding. (But maybe ask an expert, e.g. gp before getting it done.)