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... even then, the whole thing becomes rather contrived, turns into more of an exercise in imagination than processing emotion as such.

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Sounds a bit like several practices in the Tibetan models - which can easily be very contrived and mental masturbation, they can also be very powerful and/or liberating, when the conditions are right.

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I have had massive payoff from meditating on difficult emotions -as they arise-, but I seldom manage to invoce them mid-sitting.

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Just making the space every damn day matters. I'm starting to think I need to fine tune the description of that practice though.

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You mean in the sense of: opening up to negative emotions, but passing over it in silence if nothing comes up?

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But people seem to often have nothing going on. How did they get so happy? Maybe they had nice lives!

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It's not happiness; it's not-unhappiness. Low neuroticism. Personality + relative lack of childhood trauma and parental stress.

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Plenty of very happy people who are yet also basket cases. Different modalities.

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Basket case in which sense of the phrase? I’m sure you’re probably right on this - just in terms I haven’t considered before. I think often that happiness isn’t the right goal for meditators, one can be happy and sad at the same time and still feel very well & wholehearted.