He wouldn't have been a better player, he would have won more medals but he knew that.
Yes, I remember plenty he did, I always enjoyed watching him play.
I don't think he has any regrets, I've certainly not heard him express any. He knew the deal, he was happy where he was and valued that more highly than medals. Good for him. He could have moved on at any time but he never did so he was clearly happy with his choice.
Not everyone thinks like you. It's very clear that you're a glory hunter, Le Tissier wasn't, it seems he valued the friends and family and the area he lived in and, for him, that was more important.