The Vagabond

Some are known as Rogues because of nefarious deeds, others because they are strangers to upright folk. Outcast by the good and proper, they find their society among other reprobates, in the common rooms of simple folk, or perhaps even the rakish halls of the gilded elite. A rare few make themselves at home in all three. Welcome for an evening but rarely for a season, Vagabonds have learned to keep moving and find their comfort, fortune and company on the road or the seas. Some are simple and wholesome companions that warm the hearts of their fellows, while others are confident and daring leaders. Whether a charming rake or a sheltered burglar, Vagabonds forge bonds that inspire strange fellowships in spite of disparate ideals and dire circumstances.

Jack of All Trades

When you choose this archetype at 3rd level, you develop a knack for attempting feats beyond your training. You can add half your Proficiency Bonus, rounded down, to any ability check you make that doesn't already use it.

Inspiring Companion

Starting at 3rd level, during a long rest you can inspire others through storytelling, music, good food, or companionship. You and any ally to whom you render companionship during the rest become Companions until the next long rest. During a long rest, you generate a number of Companionship dice equal to your Charisma modifier (a minimum of one). These dice are d6 s. At the end of the rest, you can distribute any number of your Companionship dice amongst your Companions, or retain them for yourself. The dice last until your next long rest, when any unused dice are lost. In the interim, any one who holds a Companionship die can invoke it to bestow it on another Companion.

To do so, the holder uses a Bonus Action on his turn to choose one Companion other than himself within 60 feet of him who can hear the holder. That Companion receives the invoked Companionship die.

Once within the next 10 minutes, the Companion can roll the die and add the number rolled to one ability check, attack roll, or saving throw it makes. The Companion can wait until after it rolls the d20 before deciding to use the Companionship die, but must decide before the DM says whether the roll succeeds or fails. Once the Companionship die is rolled, it is lost. A creature cannot receive an invoked Companionship die if they already hold one or if they have a Bardic Inspiration die, and vice versa.

Your Companionship die changes when you reach certain levels in the rogue class. The die becomes a d8 at 5th level, a d10 at 10th level, and a d12 at 15th level.

Heart of the Party

Beginning when you reach 9th level, if you have invoked any Companionship dice since your last rest, you regain them after taking a short rest. Any of your Companions who has invoked one of your Companionship dice regains them when you pass a short rest in one another's company.

Well Travelled

At 13th level, you gain proficiency in any two skills or tools. Additionally, when you use the Help action to assist an ally on an Intelligence, Wisdom, or Charisma check with which you are proficient, they can add your proficiency bonus to the roll. If you are not proficient, they can add half your proficiency bonus, rounded down. Once you use this ability, you cannot use it again until you finish a short or long rest.

Rally of Heroes

At 17th Level, you gain the ability to rally your companions in the direst of circumstances. When you roll for initiative or when you or an ally are reduced to 0 hit points, you can spend a reaction to immediately invoke a free Companionship die for each of your companions within 60 feet of you or the ally that was reduced to 0 hit points. Anyone that spends a Companionship die gained in this way also gains temporary hit points equal to the result of the roll plus your Charisma modifier. Once you have used this ability, you cannot use it again until you have completed a long rest.