Any form of acceleration generates gravitational waves. The point is how strong they are. Two black holes sized ~200km (or ~30 solar masses) merging at distance ~10000km would be detected through an interferometer by a shift in one part in 1000, that is a change of ~2mm. Those are objects many order of magnitudes more massive than asteroids. So you will get gravitational waves but you wouldn't be able to detect them similar to not being able to detect the waves responsible for the orbit decay of planets.

Yes, but they will be very very very … very very very tiny, and we will not be able to detect them with LIGO+Virgo.

I'm not sure if the formula to estimate the energy we receive from the waves is (Mass1+Mass2) * SomeConstant / distance^2 or it is Mass1 * Mass2 * SomeConstant / distance^2. I'm assuming that it is the first formula. If the second one is the correct one, you must add more "very" in my first paragraph.

Yes, everything creates gravitational waves. Though at this scale we don't have equipment large enough to detect it.

Technically yes. Also, technically this is wrong:

« If it works, it will be the first time in history humans have physically changed the orbital trajectory of a space-based object. »

...because that happens every time we launch a rocket or land one.

Everything generates gravitational waves. They're just far too small to detect unless the masses involved are enormous.