re: Is it Creepy to Comment on Someone's Fitness, While in a Checkout Line?

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If they find you attractive and respond well to it, it isn’t creepy. If not, it is creepy.

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There's a strong element of truth in this... which is to say that there's no definitive answer. Women who are secure, happy, and trustful in nature will be more inclined to take an unsolicited compliment from a stranger well. And women who are more mistrustful (justified or not) or having a bad day may be more suspicious of a compliment.

I'd modify the good looking rule to be inclusive of charisma. In the same way that a person with charisma can say a lame joke and get laughs while another person gets groans or a similar dismissive reaction to the same joke, some men have a way about them-- a level of easy confidence and savoir faire-- and can read the situation and thread the needle of complimenting a lady without offending her.

Part of that, imho, is the easy confidence part. If there's any awkwardness or sense of being magnetized by the lady you're complimenting, it's more likely to creep her out. If you can casually drop the compliment in a way that it seems like you're saying it at the exact moment you're noticing it and your mind is aleady moving on to another topic without fixation (and you weren't just leering at her for several seconds before interrupting her), that's obviously preferable. The compliment has to be given freely and gracefully without expectation... then maybe it'll work.