People of that age and wealth know a lot of people who have had “work done”.
When they say, “She looks good, she really does,” I take it to mean, she’s had enough work done to still fit in and look as youthful as realistically possible.
Trump’s comment, I think was more an honest reflection about Granny Macron’s weight, which to some appears scrawny, but she’s in The Donald’s approval range.
Yes, that’s all part of it. You say “Looking good” when someone has lost weight or been working out at the gym, or some other improvement.