Here's an update:
Ditched brining and marinating/massaging due to school imposed time-restraints. Switched from SV/Confit to traditional aromatic poaching for 2H.
Cold-smoked in a improvised smoker made of a giant copper bowl with an ice bath inside, filled with pre-lit charcoal and olivewood chunks. Smooched down the flames, laid the octopus over a rack, covered and smoked for 30 min.
Sooooooooooo happy. The Olivewood we got was from a friend who lives nearby so it's a plus that it's natural & local. The improv in the copper bowl was great too. Tender, super smokey and very very olivey.