Always best to talk to him when your vibe bonus is SO HAWT!! that extra $1400 cash helps raising up a few digits and really talk to him when you raise 5 levels after Lv 20 & so on, Leveling items are (in order) Armor Hero Replicas (Headgear, Clothes, then Shoes), Octoshot Replica (same loadout as Tentateke Splattershot), Octo Tee, & Capn' Cuddlefishs Legendary Cap!