So, you gain an on-hit effect when you gain a shield. Let's say you have very high attack speed and can proc the damage immediately. Will Mordekaiser gain the damage on every hit (as he gains a shield from the damage he deals)? And will Diana gain the shield twice for one use of her W? Will Malphite keep the proc until his passive shield is broken, effectively entering every fight with extra damage? Will Overheal grant the effect all the time (provided you stay at high health)?
Also, is this run meant for tanks, for bruisers, or for damaging champions to have a tanky off-build and still do damage?