Saboteur

  You have become acquainted with the art of sabotage.  You are learning how to deal with your enemies by setting traps for them to find.  Some traps are not just meant to harm them, but to send them a message.  You are also developing a secondary sense on how to find other's traps as well.

Set Traps

3rd level Saboteur feature

  The rogue will receive and become proficient in Poisoner's Kit.  They will learn how to use it to set traps.  With the kit all they need to do is spend a round and they can set a trap on any chest, container, doorway, statue, or anything they want.  Each trap you set will require the person who encounters it to make a Dexterity save vs the rogues skill roll (poisoner's kit proficiency roll with Intelligence Modifier) or be inflicted with the poisoned condition for one minute, and suffer poison damage equal to a sneak attack.  A successful save will result in them only suffering half damage and no poisoned condition.  The rogue can use their kit to set a number of traps equal to their proficiency bonus plus one, between long rests.  If the rogue chooses to become an expert with their poisoner's kit the skill roll will improve appropriately.

  The rogue's understanding of poisons will allow them to make saving throws vs. poisons at advantage.

Specialist

9th level Saboteur feature

 The rogue has improved their saboteur techniques. They will receive the following benefits:

• Now when someone sets off one of your traps, they are not the only one at risk.  Everyone within a 10'-foot radius of the trap will be required to make Dexterity saves vs. the affects.
• The rogue can spend a "Set Trap" use to disable a dungeon feature.  Drawbridges, war machines, portals, arcane circles, are all devices that they can sabotage.  This is performed similar to the way the rogue sets a normal trap.  This requires an expenditure of a "Set Traps" use and an action.  The feature disabled by the rogue will be damaged to the point where it will take a skilled tinkerer, mending spell, or a fabricate spell to repair.  Additionally, the feature will be armed with one of the rogue's traps.
• When the rogue sets a trap, they can now choose to cause fire, piercing, or poison damage.  The piercing damage is non-magical, unless they sacrifice an appropriate magical weapon at the time they set the trap.  The rogue must state at the time they set the trap what type of damage they choose.  Only poison traps carry the subsequent poisoned condition.
• The rogue can cast the find traps spell (Intelligence-casting based) twice between short rests.
• Lastly the rogue's skill in sabotaging items allows them to always cause weapon sneak attack damage to constructs.  If they do not have advantage to the roll or an ally within 5'-feet of the target, they can use a "Set Trap" use to cause sneak attack damage.

Assess Your Enemy

13th level Saboteur feature

  The rogue has become more tactical in how they think.  They will receive a proficiency in their choice of history, insight, or investigation skills and become an expert with their poisoner's kit.  In addition to this, whenever they are within a dungeon, fortress, or enemy stronghold, they can take a minute and study their enemy forces.  It will take some time to study the enemy arms, food supply, gear, and other various clues, but after a minute the rogue will know about how many humans and humanoids are within 100-feet of them.  They will know how many, of what classes, and in which directions.  This does not tell them how powerful they are, how close (just direction/not distance,) nor does it assess non-humanoid opponents. Just numbers, types, and direction.

  The rogue can use their assessment ability twice between short rests.  If they are interrupted while studying their enemy, the use is not spent.  They may try again, once they have time to take a full minute to do so.  The rogue does not have to actually see any of their enemies to assess them, just study their gear, supplies, and surroundings, while within their territory.

History

History skill.

Insight

Insight skill.

Investigation

Investigation skill.

Deadly Traps

17th level Saboteur feature

  The rogue has mastered their trap crafting skills. Your traps now come with the following options:

• The rogue can now choose to have them cause your choice of acid, cold, lightning, or slashing damage.  Traps that cause piercing or slashing damage are still considered to be non-magical, unless the rogue sacrifices an appropriate magical weapon at the time of it's setting.
• The rogue can also use their bonus action to craft one in combat and their action to throw it like a grenade up to 60-feet.
• When you set (or throw) a trap that is going to cause the poison damage (and the subsequent poison condition,) saving throws vs. it will be at disadvantage.

This ability doesn't give you any additional uses of your traps, just more options when setting them.