Irene, the Infirm

[Crystalion]

So, feel free to speculate on how far she'll get.  This should be fun, because obviously she's not going to make it all the way.

Since you have to do the quests, and in order, the relevant must-kill-for-quest "death points" are...

Blood Raven
The Countess
Andariel

Andy herself is actually "easy" because, as an act boss, she doesn't regen (my definition of "easy" is very very loose for this odd situation). In any event, a fire/cold arrow hireling with liberal use of Town Portal (and $ for resurrection) can in principle nail her. She is also an interesting case because a v1.10 antidote potion pre-battle will help you and your rogue hireling a lot.

My impression of your skills is too high to imagine Blood Raven, as annoying as she is, will stop you.

So the real issue is whether the messy add-on monsters for the Countess and Andy are impassable (I imagine you'll tank while your rogue nibbles them to death at range)... the Andariel chamber shaman are priority kills, but I can (barely) imagine you slapping them to death.

However, in another thread, it has recently been discussed that (at least in v1.10s) hirelings do *not* get the displayed damage bonus when they do not have a weapon equiped. Therefore your hireling is doomed to have weenie damage output, as do you. Therefore my bet is that you will actually be stopped by the Countess quest.