Thought provoking question.
The World Series ring is tougher to do since most big hitters don't pitch, and definitely don't play defense at all positions at all times. It's a true team effort to win it all.
Records like "All Time Home Run Champ" isn't easy either.
Pretty tough call for me since you can get a World Series ring while being nothing more than a bench warmer. If I wasn't a starter, I wouldn't want the World Series ring since I didn't feel like I helped to earn it. Makes it hard for me to pick that one, but at the same time, I don't need to break a record to know "I am that damn good". That's something most athletes just know. Either they are, or they are not, and they certainly know it once they have been in the game for some length of time, and I know I wouldn't need an individual award to tell me that.
Very interesting question though.

Curious to watch where the votes land in this one.
Oh, and I haven't voted yet since I'm not sure what my answer is.

Yes doctor, I am sick.
Sick of those who are spineless.
Sick of those who feel self-entitled.
Sick of those who are hypocrites.
Yes doctor, an army is forming.
Yes doctor, there will be a war.
Yes doctor, there will be blood.....