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Message: <blockquote data-quote="Celtavian" data-source="post: 6836840" data-attributes="member: 5834">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.</blockquote>