Yes, that will definitely make Happy's head spin. Also, he knows how much harder it is to keep tabs on a teenager than a five year old.
I mentioned in a comment above that I imagine that Happy was still in and out of the Avengers Compound during the Blip. The Asset Management thing is more about maintaining the tech and facilities, but maybe he's also Natasha's go-to-guy? He has always had mad respect for her ever since she totally upstaged him, twice, during IM2.