The only person that can determine the easiest thing for you - is you. I had a very similar experience (minus the nipple ring - I was too chicken lol) only it was my family. None of my sibling nor DH's family had been breastfed, none of my friends at the time did. None of my mum's group did.

I took on the attitude, well I'll just give it a go. Don't get me wrong, with DD it was a struggle. A huge one. Even DH wanted me to give up, but by that stage I wanted to beat them, no matter what.

People with issues from their own pasts always try to validate themselves by getting others to agree with them and side with them. You have no issues, so you get to pick your own side.