Odyssean

Odysseans are legendary tricksters who at first glance seem like common soldiers. They carry spears and shields like any rank-and-file hoplite, but rather than moving in strict formations or honing their discipline, Odysseans hone their minds. When two armies smash together, shields bursting under the strain of a perfect phalanx, the Odyssean is the soldier who stands back and searches for weaknesses in the enemy’s defenses. Even when badly outnumbered, they may find a way to exploit conditions on the battlefield to turn the tide in the favor of their allies.
Soldiers who exhibit such a sharp mind quickly grow in notoriety and fame, but being famed for your cleverness is a double-edged sword. Odysseans are often drawn into conflicts that take them far from home, where monsters and other dangers are a constant threat. Such harrowing odysseys are the namesake of the Odyssean, who may be forced to survive several such journeys in their lifetime.
As an Odyssean rogue, you have a quick mind and you can intuit the strengths of your companions. You enjoy using your intelligence to trick your enemies and impress your friends. However, you know that you must never let your mind grow dull, for when the time comes that you are again flung into the wilderness, it will be your wits alone that save you from a gruesome death.

Vagrant Soldier

Despite your roguish demeanor, you have much of the training of a common soldier. When you choose this archetype at 3rd level, you gain proficiency with shields, medium armor, and martial weapons. Additionally, all weapons in the spear and polearm groups, such as tridents, count as finesse weapons for you.

Scrappy Trickster

Also starting at 3rd level, you gain proficiency with Charisma saves. 
Additionally, when an enemy misses you with an attack, or you make your saving throw against an enemy's spell or ability, or an enemy fails an offensive skill check against you (eg, Intimidate), you can add your Charisma bonus to the attack and damage rolls of your next attack against that enemy before the end of your next turn. If the opponent's attacks or other offensive actions fail multiple times, you can use this ability as many times as they failed. This ability also applies to spell or ability attacks if you have the option to make those in place of a weapon attack.

Clever as the Gods

Starting at 9th level, you are rarely outwitted on the field of battle. The first square you move out of each turn does not provoke opportunity attacks if you are wielding a shield. 
Additionally, on your turn, you may use your bonus action to devise a clever plan to trick an enemy. Choose one creature that you can see, and make a Charisma (Deception) roll contested by that creature’s Wisdom (Insight). If you win the contest, you and your allies who can hear you have advantage on attacks against that creature until the beginning of your next turn. You can do this as many times as you wish against different foes, but this feature cannot be used against any given opponent more than once per combat encounter.

Tenacious Survivor

At 13th level, you’ve survived through so many ordeals that you face each new challenge with grim determination. You can add your Charisma bonus to your initiative rolls. 
Also, at the beginning of your first turn in combat, you may use a bonus action to take a deep breath and expend one of your hit dice, regaining hit points equal to the roll, plus a roll of your exploit die (which does not expend a die), plus your rogue level, plus the higher of your Charisma or Constitution bonus.

Never Found the Body

Also at 13th level, if you die from any cause other than old age and no one takes charge of destroying your corpse or watching it continuously, you wake up alive and well one day later somewhere else of the DM's choice, having actually survived and drifted or been carted off by some miracle of fate or the gods. Once you use this ability, you must complete an extended rest before you can use it again.

Legendary Cunning

Starting at 17th level, you are able to instantly assess every opportunity to seize the upper hand in combat. You can make an opportunity attack every turn without using your reaction. If eight enemies were to all provoke opportunity attacks from you on their turns, you could take one against each of them.