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Two-part question, roughly in the same category.

  1. Since Guild Training is a Hybrid feat for Rogue/Assassins, is it legal or fair to take both Guild Training abilities burning two feats?

  2. Sly Flourish with Night Stalker: Guild Training.

Sly Flourish: Hit: 1[W] + Dex mod + Cha mod

Night Stalker: + Cha mod damage against any target that is adjacent to none of your enemies.

With both, do you get double the Cha mod in damage?

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To answer your second question first:

NO. In this case you do not. You missed a very important piece of the hybrid version of this feat (emphasis mine):

"You gain a bonus to damage rolls with assassin powers and assassin paragon path powers equal to your Charisma modifier against any target that is adjacent to none of your enemies." - Dragon 385

You don't get the bonus here becuase Sly Flourish is a rogue power.

As for your first. You may normally only take Hybrid Talent one time. However, if you select no paragon path you get it a second time. However, you many not take the same talent you've already taken. In this case "Guild Training" is the talent and the guild is a selection under that talent. Thus you may not take both guilds because you can't take "Guild Training" twice. (The online character builder confirms this).

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