Thanks. I'm alittle underwhelmed by Mastermind at first, until I realized that it specialized primarily in the social/skill monkey area of being a rogue, not combat. Its okay, being able to grant advantage as a bonus help action is nice I guess, being able to use another enemy as a living shield is probably the Masterminds best ability. To be honest this subclass was missed named, it should have been named Master Spy. Its not bad, but I was expecting minions of some sort.
Master of Intrigue feels like a bonus uber background.
Master of Tactics feels like a bit like a mini battlemaster.
Mastermind and Urban Bounty Hunter good well together.
A Urban Bounty Hunter Mastermind would two skills among Insight, Deception, Persuasion, Stealth, get a contact in each city, two prof out of gaming sets, musical instruments, thieving tools, you also gain 2 extra languages, prof in disguise kits, forgery kits, another gaming set, the ability to help another as a bonus action up 30 feer away in combat, gage someones char/wis/int/class level/personality traits from 1 minute observing them in conversation.
So an example a Half Elf High Urban Bounty Hunter Mastermind would be at level 3.
Languages Elvish, Common, Primordial, Mulhorandi, Celestial, Thieves Cant Tool Profiencies: Cards, Dragon Chess, Thieving Tools, Disguise Kit, Forgery Kit, Fiddle Skills: Deception, Perception, Persuasion, Arcobatics, Insight, Invistiagion, Religion, Intimidation. Racial Traits: Darkvision, Fey Ancestory, Skill Versatility, Expertise, Sneak Attack, Thieves Cant, Cunning Action, Master of Intrigue, Master of Tactics. For expertise Persuasion and Insight.
This makes for a major Urban based skill monkey, with a bunch of laugages, skills, profiencies, expertise, contacts in every major city, the ability to fake accents, the ability to see in the dark, resistant charms, immune to sleep spells, musical talent (drums). And it would only get better as one levels.
Its a spy with just a pinch of a warlord feel.
Master of tactics can be used in combat to help someone attack, escape a grapple, make a saving throw, use a skill in combat, help a fellow Rogue gain advantage in order to sneak attack (it seems weirdly fitting that Mastermind is the Rogue subclass that benifits other Rogues in the party the most).