Uh, would we really be waiving those flags from the moral high ground here, or just from somewhat higher ground than Russia?

I'm not sure Gilbert Baker is understanding this exactly right. Waving the pride flag at the Olympics wouldn't serve to cover up Russian atrocities or serve as an endorsement of repression, but rather would be a protest against those things, and at this point I would think that most people would recognize it as such...

No. We wouldn't send athletes to the summer Olympics in Saudi Arabia, why should we send them to winter Olympics in Russia?