The total mass/energy of the suspended object goes like
$$M(r)=\sqrt{g_{00}(r)} M_\infty$$
so near the event horizon, this goes to zero. Consequently, almost 100% of the $E=M_\infty c^2$ latent energy may be extracted by lowering it near the horizon.
If you're willing to wait for the black hole to Hawking evaporate, you may obtain the whole $E_{\rm BH} = M_{\rm BH}c^2$ in the form of radiation. However, this energy isn't coming from a particular object that you lowered; it comes from all of them, from converting the black hole itself to energy.
Even if you wanted to attribute the energy from the "extra lowering" to the particular suspended object, you won't be able to get more than $E=M_\infty c^2$ out of the object. The first formula of this answer is still true. So if you keep the object at the same "depth" but you allow the black hole to shrink a bit so that the suspended object is suddenly further from the event horizon, it means that $g_{00}$ (the red shift factor) will be increased again, which will reduce the energy of the suspended object.
In other words, if you want to keep the (highly reduced) energy of the suspended object constant (near zero), you should allow it to keep a small distance from the event horizon. It means that if the black hole shrinks by Hawking evaporation, the suspended object will have constant energy if it is lowered as the black hole shrinks.