Short Rogue (V2)

Short Rogues have been made fun of, slandered, and kicked around for long enough. Instead of moaning about, they spent their time plotting their revenge, and showing that they are different. dangerous combatants, they are also skilled with making money and using that money to benefit themselves. Non short races have been seen as short rogues, but they are not common at all. If you are going against a short rogue, you should surrender early before things get worse for you.

"Cute"

When rolling initiative, if you are fighting a creature that is at least one size larger than you, you may add your charisma modifier to your initiative.

Whilst going against creatures that are 2 sizes larger than you, roll stealth, if that roll is higher than that creatures passive perception, then you automatically gain sneak attack against that creature, and they have disadvantage on attacks against you. If you are in any creatures space, you have advantage against them.

If you do not have proficiency in persuasion, you learn it and get advantage on persuasion checks against creatures larger than you. If you already have the proficiency in persuasion, then you gain expertise. You may also get advantage on persuasion checks against creatures larger than you.

Gold Sense

Starting at 9th level, you get an uncanny link to valuables. During a short rest, you may choose to use this feature to learn of any valuables (100 GP+) in an one mile radius, to a maximum of 5 items (at least 1 item above 10,000GP+ if it exists, 1 item worth 5,000GP, and 3 items worth above 100GP) This counts as a light activity as to also gain the short rest benefits. 

Precise Carelessness

Starting at 13th level, you start to live fast but still be hyper focused, as a result you gain +10 to movement speed. Your focus to take out an enemy lets you score a critical hit on a 19 and 20 on creatures at least one size larger than you.

Short Rage

Starting at 17th level, You can force your target to make a perception check against your stealth check.  If they do not detect you, then you automatically double your damage.