I'm currently doing single Assassin solo run (very fun).

 

I'm wondering however, what is the easiest way to trigger "Deathblows"?  

 

https://pillarsofeternity2.wiki.fextralife.com/Deathblows

 

Is there any item(s) to aid in this so I can save resources?

Probably upgrading Crippling Strike to Debilitating strike.  It adds Distracted Affliction to Crippling Strike which already Hobbles.  1 Guile, 2 Afflictions, Should give you Deathblows.  Either that, or flank target + any Affliction. 

 

EDIT:  Atleast that's what ole' Jack Burton told me.

Edited May 18, 20187 yr by Ganrich

Persistent distraction will give you flanked so you don't need to upgrade anything but you'd still need to use crippling strike.  If you were multi classed you could get enervating blows from monk but then it'd be endgame before you got deathblows...

Probably upgrading Crippling Strike to Debilitating strike.  It adds Distracted Affliction to Crippling Strike which already Hobbles.  1 Guile, 2 Afflictions, Should give you Deathblows.  Either that, or flank target + any Affliction. 

 

EDIT:  Atleast that's what ole' Jack Burton told me.

There's a passive ability that makes you perma distracting. So just any active ability with affliction will do to set it up.

I forgot about that passive.  Good call.

If you have a Chanter (either as party member or as multiclass option) with the weakening chant plus Persistent Distraction you can deal Deathblows without the use of an active ability that would cost Guile or any other resource. That the least micromanagement-intense, "laziest" way to unlock Deathblows that I know of.