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I'm trying to build an optimized character for a 5th edition D&D campaign and I really like the crossbowman fighter concept, but I had considered dipping into rogue for at least 3 levels to pick up sneak attack damage and the assassin archetype. Would this be a good idea, or would it just be better to go full fighter in order to get all of my Extra Attacks?

I'm trying to optimize for maximum damage.

I've chosen Battle Master for the Fighter archetype, as it seems to be the most useful for this particular type of build. Survivability isn't a priority over damage, but I'll take it where I can. This particular game is starting at 3rd level and may very well last until 20th.

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I Do Not Recommend Dipping Assassin

The three levels of Rogue will mean you lose the fourth attack from Fighter 20. We'll ignore the actual crossbow in use, because we can compare the average damage of two Sneak Attack dice (7) to the damage bonus from Sharpshooter (10, and you are taking Sharpshooter, right?). Combine that with that Extra Attack also including the base damage for the weapon and your attribute, and a few dice of Sneak Attack keep getting smaller and less relevant.

By taking those Rogue levels, you also lose out on the L18 fighter Feature (in the case of Battlemaster, that's d12s for your Superiority Dice) and the L19 ASI.

What do they get you? Not much. We've already determined Sneak Attack itself is not worth it (and we didn't even consider all the conditions that need to be in place to get a Sneak Attack in the first place). Assassinate seems good on paper, but is pretty weak in practice, especially what appears to be the bigger benefit. The problem comes that Surprise is difficult to arrange on a regular basis - it's not something you can force.

I Do Not Recommend Assassin At All

Honestly... I can't make a general recommendation for Assassin at all. Unless you know your DM is going to reliably and regularly set up the conditions for it's abilities to work (Infiltration Expertise and Imposter are highly DM-dependent, too), it simply isn't worth the investment.

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    \$\begingroup\$ I've found that Assassin is mostly good if you want to run a solo campaign, or if you have a DM who is up for running stuff for you apart from the rest of the group. Otherwise...the situations in which an Assassin is actually useful involves very large blocks of time where the rest of the party is sitting there doing nothing. \$\endgroup\$ – guildsbounty Jan 18 at 16:55
  • \$\begingroup\$ Okay, thank you very much for your reply. Are there any multi dips that -would- be better for optimization or would pure fighter still be better overall? \$\endgroup\$ – Crossbow Enthusiast Jan 18 at 17:18
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    \$\begingroup\$ @CrossbowEnthusiast now that is a huge other question that would need more information even to begin to answer. Since we can only answer 1 question per post (and never in the comments) you are welcome to try to ask it as a new question, but note that we are going to need to know a lot of details about your goals and restrictions in order to answer it. \$\endgroup\$ – Rubiksmoose Jan 18 at 17:43
  • \$\begingroup\$ Alright. I'll try and ask in another post, then. Thank you! \$\endgroup\$ – Crossbow Enthusiast Jan 18 at 17:47
  • \$\begingroup\$ @CrossbowEnthusiast no problem! before you ask take a look at this post and answer as many questions from that in your question as you can (all of them preferably). \$\endgroup\$ – Rubiksmoose Jan 18 at 17:50

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