Black Marketeer

"Everything has a price."  These words ring true in your heart and you know that there is always a buyer for any item.  You specialize in finding sellers of unconventional wares and connecting them with interested buyers.  You can strike deals with everyone from nobles looking for "re-acquired" art or the services of an assassin, to a cult member seeking relics of lost power.  Who it is doesn't matter to you, so long as they know the universal language of coin.  You can read the ebb and flow of the stormy underground markets to know when to buy and sell, or when to stay home.  As long as there are goods to move you can always find a guy but it might cost a lot on a bum day.

Ear to the Ground

You have finally made the needed connections with the right people to keep your thumb on the pulse of the underworld's markets.  You can find black market connections in any community large enough to support an underground and you can buy and sell any item at any time at the market standard of 2x purchase price and 0.5x sale price.  You can also offload stolen items in this manner at an item per day rate equal to your rogue level.  In addition, you are capable of appraising items for their market value.

Market Savy

Starting at 3rd level you have dealt with enough underworld clients that you have a feel for the markets and how to read their volatile flow.  When you go to connect to the black market you can choose to roll 1d4 on the Black Market Table and for the rest of the day, those price multipliers will be in effect.  Once you choose to roll these modifiers take effect and cannot be rerolled until after a long rest.

Die Roll	Black Market Table
1	Buy items at 0.75x value and sell at 1.25x value
2	Buy items at 1x value and sell at 1x value
3	Buy items at 2x value and sell at 0.50x value
4	Buy items at 4x value and sell at 0.25x

Smuggler

Starting at 9th level, you gain advantage on Sleight of Hand and Deception attempts to conceal illicit goods or true identities when dealing with authorities.

Use Magic Device

By 13th level, you have handled enough magical items that you can improvise their use even when they are not intended for you. You ignore all class, race, and level requirements on the use of magic items.

Always One Step Ahead

You've been at this game for a long time.  When you reach 17th level, you have become adept at avoiding sting operations and quickly escaping danger. You can move to the front of the initiative order during the first round of any combat. You can then take either the Disengage or Dash actions. You can’t use this feature again until you complete a short rest.