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Main advantage of air launch is that you can better match your target inclination or perhaps even orbit timing - just drop the rocket at the right time in the right direction over the ocean. With a fixed launch site you always need to adjust for some difference of your point of origin versus the orbit you want to achieve.
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How big a trebuchet would be needed to chuck a cubesat directly into LEO?
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cubesat + small rocket. Orbital mechanics require a burn at a later time in the orbit, to avoid coming back to say hello again to Mr. Trebuchet (Ignoring Earth's rotation)
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100 or 200 km tall at point of release ought to do it.
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It helps a bit more than you imply, though: if you can launch from a higher altitude, you have less atmosphere to plow through. That lets you use more of your propellant to speed up instead of to push air out of the way.
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That isn’t very helpful considering rocket launches only spend a few seconds in atmosphere mostly going vertically to get above the majority as quickly as possible .
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You've just got the problem of building a fixed wing aircraft which can carry your rocket full of explosive propellant, successfully release it pointing in the right direction and then get the hell out of the way....
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You're extremely limited by the amount of mass you can even launch from a mothership aircraft.

There's no future in this idea outside of small sat, and probably not even there.

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