Heist Movie

Always prepared and at all times one step ahead, the Heist Movie rogue is capable of determining exactly what they'll need in any given job, exactly when they'll need it. Nothing surprises this rogue, and it shows. It really shows. Some rogues of this archetype use their powers for greed, trying to steal priceless artifacts and get away without getting caught, or to reveal to the rest of the crew that they were a double-triple agent the whole time, and was playing them all like fools from the start. A select few, however, use this power for good, having a tool belt that always has precisely what they need, be it shark repellant, a balloon animal, or a gun.

Whatever they use their unique skills for, one thing is for certain: they always come prepared.

Flashback

When you choose this archetype at third level, you gain the ability to flash back to any point of time within the last month, or to a specific plot-relevant point in time if your DM allows it. While flashing back in this way, you may choose to orchestrate one of the following options:

• You obtained a non-magical common item, tool, or weapon of your choice. You may choose an item of a higher rarity or a specialized tool that may or may not exist at your DM's discretion. 
• You obtained a map, floorplan, blueprint, or diary of your choice within the DM's discretion. It may include the entrances to secret rooms, stashes, or crawlspaces. Additionally, you could obtain another document that you choose, within the DM's discretion.
• You paid off a minion, staff-member, guard, or official so that they would be favorable to you and your party. This person might assist in combat, but is not willing to risk their life for you. Additionally, they may have been instructed to retrieve a specific item such as a keychain for the party to use.
• You establish rapport with a creature of your choice. You may have served time in prison with them, done a job with them, or otherwise have history with them that may make them favorable towards you.

The DM may decide that an effect you choose requires you to make a skill or ability check to succeed, and a failed check may result in a negative outcome. You may use this feature an amount of times equal to your proficiency bonus. You regain all expended uses after a long rest.

Psychoanalyze

Beginning at third level, your immense preparation and experience allows you to outsmart any creature you encounter. You gain proficiency in Wisdom (Insight) checks. Additionally, as a bonus action on your turn, you may make a Wisdom (Insight) check against a creature of your choice within 60 ft. of you, contested by a Charisma (Deception) check done by them. On a success you can determine two of the following characteristics:

• How many hit points they currently have;
• What guild, organization, religion, or cult a creature serves, if any;
• What a creature's AC is;
• How many class levels a creature has, if any;
• How many rogue levels a creature has, if any.

Additionally, on a success, you gain advantage on the next weapon attack you make against that creature within the next minute. You may use this feature a number of times equal to one plus your wisdom score, minimum of one time. You regain all expended uses on a short or long rest.

Double Agent

Starting at ninth level, you are able to play all sides of a conflict masterfully. You must spend seven days and 50 GP to be considered a member of an organization that you know of, provided you have a way to speak with at least one of their dedicated members. If the organization is actively hostile to you, you must spend 200 GP instead.

Your ruse is indiscernible unless you give a creature a reason to suspect you to be an imposter. If a wary creature detects something is amiss, you have advantage on Charisma (Deception) checks made to avoid detection.

While considered a member of an organization, you may use your Flashback feature to dramatically reveal your status as a double-agent and gain advantage on attack rolls against creatures of the organization you were feigning allegiance to. Once you do this, you are no longer considered a member of this organization and may not use this feature to feign allegiance to this organization again.

Fortuitous Stash

Starting at thirteenth level, you are never caught unprepared. If you are unarmed, you may use your Flashback ability to reach into the nearest container, under the nearest table, or any similar space and pull out any non-magical weapon of your choice. Additionally, you may choose to pull out a single magical weapon of the DMs choice.

If you create a weapon in this way, you must also come up with a feasible solution as to how you obtained it, but not how it got to the place you pulled it from. If you purchased the weapon, you must still pay for it.

The Long Con

Starting at seventeenth level, your planning knows no bounds. When you roll initiative, you may choose to use your reaction to expend one use of your Flashback ability and force up to 6 creatures of your choice that you can see to make a Charisma saving throw. On a failed save, they become friendly to you and your companions and join your side in combat, having been revealed to be double agents working for you.

If you choose a creature that could not have been a double agent, such as the leader of an organization, a lich, or some other similar creature, the DM may force you to choose a different target. Animals and unintelligent creatures are not immune to this ability.

The DC for this ability is equal to 10 + your proficiency bonus + your wisdom modifier. Once you use this feature, you may not use it again for 30 days.