The balloon does not have negative weight. The balloon rises because it’s *buoyant* – that is, it weighs less than the air around it, so the air around it can push it out of the way in order to sink. It’s no different from floating in water: something heavier than water can push it out of the way and sink, while something lighter than water gets pushed out of the way by the water and floats.
The weight (=force from gravity on the balloon itself alone) is still positive, but there’s another force that is greater than its weight, and the *total* force on the balloon points upward.
As for how you’d measure this force, the simplest way is to just attach a string to the balloon, let it rise until the string is pulled taut, and then measure the tension in the string.
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