I really think that the best guide to playing assassins is actually playing one, BTB, from level 1.
A starting assassin has no real thief skills, marginal HP, and only the option of adding a shield to their marginal leather armor. They can't hire hirelings and do the "level 1 fighter as the leader of men, a sergeant in charge of a squad" strategy. The assassins guild may be helpful, but I'd expect most help to have strings attached. They also have tough ability score requirements and incentives that make prioritizing DEX unlikely; that reduces AC, surprise, and dual-wielding possibilities. These limitations prevent them from using traditional fighter or thief strategies. What do they have?
Bonus XP and GP for conducting assassinations.
Low level targets are reasonable and pay a decent amount of dough. They also get bonus XP for doing the deed. This is even possible in a megadungeon setting; I can imagine missions like, "Assassinate the goblin slinger that hangs out with a band of thugs on level 2 of the dungeon." Depending on the campaign it may be possible for the assassin to power up through the lower levels.
Fighter-quality weapon selection.
While they only get three choices, I think fighter-quality weapons are very worthwhile. I think every assassin should have at least one back-stab capable weapon, so that probably means a long, short, or broad sword. The other two should probably include some sort of polearm; long weapons strike first, and 1d10 damage is enough to kill many low-level monsters. A polearm also lets you fight from the second rank and avoid heavy combat. The other should probably be some sort of hurled or projectile weapon. If lucky enough to have 17+ DEX, then a hand axe or dagger seems wise for dual-wielding.
Given that BTB (non-UA) only fighters get bows, it is a pretty big deal to be able to use a bow. Thieves don't get them, BTB (PHB only). Same thing for polearms. An assassin that chooses proficiencies unwisely is giving up a major strength.
Poison usage.
The DMG gives guidelines for different types of assassin poisons. Some are quite reasonably priced. While at first blush they seem lackluster, remember that 10 HP of damage is basically the same as doing 3 HD of damage. A poisoned arrow might be enough to slay an ogre outright, which is pretty impressive.
Disguise capability.
I don't have my PHB in front of me but I believe that even low-level assassins can use their disguises as a class function. This makes INT important, as speaking a wide variety of languages will be helpful for impersonating many different kinds of foes. It also makes CHA important, as getting good reaction rolls up front will be helpful.
Basically, my bottom line is that an assassin character has few mechanical advantages over thieves. The real key, if you play BTB, will be player creativity and tactical sense. Using things like disguises or setting traps will be the key to success, and that requires both player savvy and roleplaying skill to get away with. The only other option is to be relegated to second-rate fighter status, standing in the back with the polearm. While some situations may call for that (and while it may be the best of poor options in some tactical situations) I don't think many parties will be happy dragging along such a character. To be useful the player will have to use their creativity (if allowed by the DM in the campaign), or better yet, an extremely shrewd and opportunistic tactical sense.
Many players will try to be a fighter, charge in, and die. Others will try to be a thief, and realize that they are not sneaky or good at scouting. With the right DM, campaign, and player, an assassin could be enormous fun. I think they would shine in a smaller party, especially. While I would require them to be evil, evil doesn't necessarily mean dumb.
This is why I say the best education is playing BTB: players who can't hack it will die and try another class that they are better suited for. Likewise if the campaign is unsuited for them then that will become obvious quickly as well. Assassins are an advanced class meant for advanced players, similar to the other sub-classes.
Additionally: I would point out that an elvish assassin is quite possibly highly effective with a less skilled player, because of their inherent racial bonuses to surprise. This could mean lots of backstab and/or assassination attempts, depending on your DM. While more approachable for a less shrewd player, I am not convinced this is the best way to go; long term there is a level cap, and moreover there is no Raise Dead for elves that bite the dust so eventually you'll get unlucky, fail a save, and die for good.
A starting assassin has no real thief skills, marginal HP, and only the option of adding a shield to their marginal leather armor. They can't hire hirelings and do the "level 1 fighter as the leader of men, a sergeant in charge of a squad" strategy. The assassins guild may be helpful, but I'd expect most help to have strings attached. They also have tough ability score requirements and incentives that make prioritizing DEX unlikely; that reduces AC, surprise, and dual-wielding possibilities. These limitations prevent them from using traditional fighter or thief strategies. What do they have?
Bonus XP and GP for conducting assassinations.
Low level targets are reasonable and pay a decent amount of dough. They also get bonus XP for doing the deed. This is even possible in a megadungeon setting; I can imagine missions like, "Assassinate the goblin slinger that hangs out with a band of thugs on level 2 of the dungeon." Depending on the campaign it may be possible for the assassin to power up through the lower levels.
Fighter-quality weapon selection.
While they only get three choices, I think fighter-quality weapons are very worthwhile. I think every assassin should have at least one back-stab capable weapon, so that probably means a long, short, or broad sword. The other two should probably include some sort of polearm; long weapons strike first, and 1d10 damage is enough to kill many low-level monsters. A polearm also lets you fight from the second rank and avoid heavy combat. The other should probably be some sort of hurled or projectile weapon. If lucky enough to have 17+ DEX, then a hand axe or dagger seems wise for dual-wielding.
Given that BTB (non-UA) only fighters get bows, it is a pretty big deal to be able to use a bow. Thieves don't get them, BTB (PHB only). Same thing for polearms. An assassin that chooses proficiencies unwisely is giving up a major strength.
Poison usage.
The DMG gives guidelines for different types of assassin poisons. Some are quite reasonably priced. While at first blush they seem lackluster, remember that 10 HP of damage is basically the same as doing 3 HD of damage. A poisoned arrow might be enough to slay an ogre outright, which is pretty impressive.
Disguise capability.
I don't have my PHB in front of me but I believe that even low-level assassins can use their disguises as a class function. This makes INT important, as speaking a wide variety of languages will be helpful for impersonating many different kinds of foes. It also makes CHA important, as getting good reaction rolls up front will be helpful.
Basically, my bottom line is that an assassin character has few mechanical advantages over thieves. The real key, if you play BTB, will be player creativity and tactical sense. Using things like disguises or setting traps will be the key to success, and that requires both player savvy and roleplaying skill to get away with. The only other option is to be relegated to second-rate fighter status, standing in the back with the polearm. While some situations may call for that (and while it may be the best of poor options in some tactical situations) I don't think many parties will be happy dragging along such a character. To be useful the player will have to use their creativity (if allowed by the DM in the campaign), or better yet, an extremely shrewd and opportunistic tactical sense.
Many players will try to be a fighter, charge in, and die. Others will try to be a thief, and realize that they are not sneaky or good at scouting. With the right DM, campaign, and player, an assassin could be enormous fun. I think they would shine in a smaller party, especially. While I would require them to be evil, evil doesn't necessarily mean dumb.
This is why I say the best education is playing BTB: players who can't hack it will die and try another class that they are better suited for. Likewise if the campaign is unsuited for them then that will become obvious quickly as well. Assassins are an advanced class meant for advanced players, similar to the other sub-classes.
Additionally: I would point out that an elvish assassin is quite possibly highly effective with a less skilled player, because of their inherent racial bonuses to surprise. This could mean lots of backstab and/or assassination attempts, depending on your DM. While more approachable for a less shrewd player, I am not convinced this is the best way to go; long term there is a level cap, and moreover there is no Raise Dead for elves that bite the dust so eventually you'll get unlucky, fail a save, and die for good.
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