you can't take only one lvl of an archytype if you take more lvls in it i.e. rogue and barb. You get you stick with it.
oh, sorry I didn't realize you were doing it by when you would take lvls. I thought that was just what the end would look like.
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Well obviously the bane of all melees will be positioning. You're hooped against flyers. Max HP will help with your staying power but don't underestimate the FC bonus HP. Also you are gonna need AC AC AC and eventually some kind of concealment miss chance to help with your staying power.
Other than that not sure if power attack fits the DW dagger motif. PA scales better with 2 handers, and high % crit weapons, You'd be better off with things like Combat Expertise, Dodge, Mobility. Remember you are going to be in the dirt face to face with the enemy you NEED staying power.
I would suggest both of you get the Distracting Attack rogue talent and Sap Master (which requires Sap Adept first) for some great synergy. I'm not too keen on the knifemaster, I prefer the Thug and Rake archetypes. I'd also suggest the Warslinger Halfling racial variant to reload a sling as a free action. May or may not synergize with your melee DPR, but having a ranged weapon you can full attack with on the opening round of combat surely isn't a bad idea. I suppose if dipping bard you could just use a longbow, though...
Note that the sling could be used with Sap Adept/Master if you took the Bludgeoner feat as well (said feat would also allow Sap Master/Adept to apply to a bow if using Blunt Arrows from the APG).
The only teamwork feat I'd recommend is Lookout. It's just a shame you have to be adjacent, surely within 10, 15, etc... ft could've been ok? In any case, Lookout + both of you being stealthy = lots of combats that you start off with a full round action surprise round.
Benefit: A rogue with this talent can make sneak attacks with subtle flourishes that disorient and distract her enemy. When she hits a creature with a melee attack that deals sneak attack damage, she can forgo the additional damage to cause the creature to become flat-footed against one target of her choosing until the beginning of her next turn. The rogue cannot designate herself as the creature gaining the benefit of this talent. Creatures with uncanny dodge are immune to distracting attack.
You knock the sense out of foes with a well-timed surprise attack.
Prerequisite: Sneak attack +3d6, Sap Adept.
Benefit: Whenever you use a bludgeoning weapon to deal nonlethal sneak attack damage to a flat-footed opponent, roll your sneak attack dice twice, totaling the results as your nonlethal sneak attack damage for that attack.
Halflings are experts at the use of the sling. Halflings with this racial trait can reload a sling as a free action. Reloading a sling still requires two hands and provokes attacks of opportunity.
This replaces the sure-footed racial trait.