Different Thieves

This is sort of based on the T&T Rogue and that "good at/bad at" system someone put together (I forget who?) and Telecanter's famous rogue but adapted for a FLAILSNAILS style experience and with an eye on this setting I've been creeping toward. Normal Thief proficiencies/restrictions/XP thresholds/saves/HD.

Robbers

Each level choose 1 thing you are Skilled at. Whenever you would roll to do that thing, you roll an extra die of whatever kind you're rolling (usually a d20 or d6). You may always elect to take the higher roll or not, for the rare situations you might want to roll lower. If more than one roll is successful then the DM may either improve or multiply your success effect or grant you some additional boon, at their discretion.

At first level and at every even-numbered level you may either choose two Skills or one Expertise, which is a Skill that grants you two extra dice.

At third level and at every odd-numbered level you become capable of using a different kind of magic item. First comes scrolls/potions, then rings/clothing, then weapons, then armor/shields.

At first level whenever a Robber employs a non-combat skill while engaged in combat their allies EACH gain a damage bonus for that round equal to the Robber's level. If the Robber is off opening a safe during the gnoll fight then this doesn't apply.

Thieves who reach level 9 do not choose a normal Skill that level but instead gain either an Expertise in an existing skill or Supremacy in an existing Expertise. Supremacy grants an additional die as well.

At level 9 a Robber decides whether to become a Fighter or Magic-User and levels up from there using the Robber XP chart, gaining any abilities by-level as if they were the new class and the capability of using any magic items they can't use already. She no longer gains Skills, Expertise, or Supremacy. You do, however, gain a new ability score: Fortune. Once per day per level of Fighter or Magic-User the Robber possesses, they may take their Fortune roll in place of an attack, damage, or saving roll.

So what are Skills? They're something any character may attempt but they get only one die per shot, while Robbers get up to 4. This includes metagame concepts like the wandering monster check (which you can chalk up to the Robber's evasiveness) , initiative, surprise, navigation through wilderness with a map, etc. It includes pure combat elements like to-hit rolls, maintaining a grab, two-handed fighting. It includes old skills like Rope Use, things like LotFP's Architecture, 4e's Endurance, 5e's Persuasion, and Cooking and Herbology and Mapmaking and Tattooing and Seduction and Camouflage and Smithing and Disguise and Impressions and Handling Your Ale.

If you ask for something weird for a Skill it's up to the DM, who always gets to define when your Skills are appropriate. Don't go thinking you can just take Skills in Fighting and Stealing and call that lunch.

Strange Monks

Boxer


HD: as Dwarf
Save: as Dwarf
Attack: as Dwarf
Advance: as Dwarf
Requirements: No ability score lower than 9 (or qualifying for the class with a Requirement Roll)

• Boxers may use any armor and may use any weapon. They may not use a shield but gain a shield bonus if holding a two-handed weapon.
• A Boxer's stances and techniques are limited by any armor, however. When a Boxer is the subject of an attack, hazard, or effect targeting their AC the Boxer rolls 1d20 plus their Wisdom bonus. If their result is higher than their own AC, the attack fails or is mitigated. If the Boxer's result is higher than both their own AC and the aggressor's to-hit result, the Boxer may make an unarmed attack as a free action. In this way an unarmored Boxer is always a safer, more fluid fighter.
• A Boxer may also fight unarmed, doing less damage overall but gaining an added benefit. A Boxer's unarmed damage is equal to 1d3+Level. This unarmed damage is considered to be whatever type of damage the Boxer's target is most vulnerable against, including elemental damage or silver or holy water. Enemies who can only be harmed by magical attacks will be harmed by the Boxer's unarmed strikes.
• At each level from 1 to 9 you may choose to make an additional unarmed attack per round or elect to learn a Special Move. Special Moves can be performed on your initiative and may duplicate the effects of a single piece from the Equipment List for a round. There is no limit to how weird you can get with this but a movement technique will always take place during a movement phase, an attack effect will always take place during attack phase, etc. This extends to armor and weapons; while armor bonus gained this way will not count against you for your evasion/counter rolls, the higher damage potential from unarmed damage duplicating weapon effects will NOT benefit from your normal unarmed damage's ability to bypass resistances and exploit weaknesses.
• At level 9 Boxers become Masters. They may elevate level 0 characters to level 1 Boxers with only a day's instruction. Additionally they must choose to walk the path of perfect body, perfect mind, or perfect spirit.
• Mind- At each level starting now you may pick one Skill or Language from your game and consider yourself 95% proficient in it, only failing in your attempt on a 1/d20.
• Body- At each level starting now you reduce all physical damage, including from poison or elements or falling or other hazards, by half your level.
• Spirit- At each level starting now you may choose one spell of any level from the list of your campaign. You may cast this spell once, and you are forever immune to its effects from other casters.
• Boxers may advance to level 16. At level 16 you WILL be killed and one of your pupils will gain +5 levels in order to seek their revenge.