Azurewraith
Explorer
You didn't take Expertise in Perception? That is an essential scout skill. It doesn't help much if you're getting ambushed or destroyed by dangerous traps. You're a Halfling which means no Darkvision, thus your stealth will be nearly useless since you'll likely have to employ a light source to Stealth which negates the advantages of Stealthing. Even with Darkvision, when Stealthing absent light we'll have a reduction in Passive Perception of 5 due to shadowy light. Without darkvision, our scout will be a sitting duck. No Acrobatic Expertise to resist grapple is less of a problem because you'll be ranged. No expertise in Thieves' Tools for disarming traps could be a problem, then again traps don't come up a ton. Investigation is not bad depending on how Flamestrike runs that skill and if he allows Passive Checks.
For an assassin, you're definitely hamstringing yourself by choosing Halfling with no darkvision and no Expertise in Perception. The lack of Darkvision in 5E for a PC that relies on Stealth is a huge disadvantage. Given you have a decent Charisma, you may almost want to optimize by taking some levels of warlock to obtain Devilsight. This will make you a far more effective Assassin.
Just an FYI that if Flamestrike's encounter design is as ruthless as he has made it sound, you may get hammered quickly lacking the advantage of seeing the enemy first.
Ah the perception and tools is my bad lingering house rules in my head we where using investigation for trap finding and sleight of hand for disarming old habbits and what not. As for the 2levels of lock that could be a plan I was looking after the kids while knocking this up. Didn't think through all the options just assumed some kind soul would cast darkvision on me. Don't dnd with parental responsibility folks it don't mix. I'm assuming its cool to flip investigation for perception and hands for tools if that's how where running it seen that wep not started. I wasn't concerned about the grappling as they would need to get close by that point the caltrops and ball bearings gone out and I'v found a hiding spot somewhere.
Frigging house rules getting stuck in my mind grrr. Have to see what [MENTION=24449]FLA[/MENTION]nestrike says its about 6am for him though(if I remember timezone right)