Guerrilla

Some call them freedom fighters and some call them terrorists. Their tactics maybe unconventional and dishonorable but what choice do they have? Their enemy is well armed and well funded and would crush them in the open field. Some guerillas wish to dispose of an evil tyrant, some enjoy striking fear in the hearts of their fellow man, and some simply want to fill their pockets from the kings' coffers. Whatever their reason for fighting, a guerrilla is a formidable opponent to even the mightest of empires. 

The Occupier

Starting at 3rd level, you begin your guerrilla war against your oppressor. Choose an organization you have come into contact with in the past to become your sworn enemy. Your sworn enemy can be a government, guild, criminal enterprise, or another type of powerful and organized group determined by your DM. Sworn enemies count as favored enemies.

You have advantage on Charisma (Intimidation) checks on sworn enemies when trying to extract information from them as well as on Charisma (Persuasion) checks when asking anyone to betray or sabotage your sworn enemy.

Whenever a sworn enemy makes an attack roll against you they must also roll a d4 and subtract the number rolled from the attack roll.

The Homeland

Starting at 3rd level, you can leverage your familiarity with a certain kind of terrain against your enemies. You gain an additional favored terrain type. You become proficient in Dexterity (Stealth). You have advantage on Dexterity (Stealth) checks while you are in favored terrain.

You can spend an hour to sabotage up to 120 feet of favored terrain and make it difficult terrain. This terrain does not count as difficult for you or anyone you teach to bypass the sabotage. 

Tactical Retreat

Starting at 7th level, you can make it difficult for your enemy to keep you pinned down. Opportunity attacks made against you have disadvantage. If an opportunity attack made against you misses your walking speed increases by 10 feet until the start of your next turn.

Hit and Run

Starting at 11th level, you are a master at laying ambushes and striking first. You can give yourself a bonus to your initiative rolls equal to your Wisdom modifier. While In favored terrain, you and your allies have advantage on initiative rolls and sworn enemies have disadvantage.

Infamous Revolutionary

By 15th level, your deadly efficient tactics have created an air of dread and mystery around the mear mention of your name. Each sworn enemy that is within 120 feet of you and aware of you must succeed on a Wisdom saving throw or become frightened for 1 minute. A creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success.

Disappear into the Wilderness

At 15th level, you become so familiar with the wilds that you can make it nearly impossible for anyone to find you within their bounds. As an action, you can make yourself invisible for 1 hour while in favored terrain.

Once you use this feature, you can’t use it again until you finish a short or long rest