D&D 5E Help with planning level ups.

Pensivetoast

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Hopefully I can pick the brain of some more experienced players here.

My home group recently resurrected our D&D game. The first thing we had to do was change over from 4th to 5th. For most players this wasn’t an issue, but my old 4e character class was the Assassin (of which there was no equivalent in 5th ed) so I wound up with a Rogue2/Bladelock3. (16 str, 18 dex, 15 Cha for key stats)

Due to conversion issues, our GM let us keep our feats, so I have Mobility, which works well with the character. Now, for my next level, I’m going to grab Rogue/Swashbuckler. I like the boost to initiative and sneak attack, though the disengage part is offset by mobility (for the better). However, after that I’m at a bit of a loss.

On one hand, my next two level ups are both Lvl 4s, so I can get stat boosts and/or feats. If I go feats, I’m looking at Warcaster so I can Eldericht Blast even while armed. And then Dual Wielder so I can finally start using a bonus action to attack with an offhand weapon (Current pact blade is a Rapier) and get a small AC boost (currently 17 with studded leather). However, needing to sink two levels into feats seems a little much.

On the flip side, I can just take 4 points of Dex over the feats, and get all the appropriate bonus of 22 Dex. Or add a point to Cha, or other stat shenanigans. Or I can mix and match feats and stats.

Keep in mind due to party makeup, my character is considered one of two front line fighters/damage dealers (the other is a monk.)I find I’m really enjoying the versatility these classes have given me. The table is also more of a ‘Role play’ as opposed to ‘Roll Play’ game. That being said, we are doing the Princes of the Apocalypse module, so I have no doubt it’ll be combat heavy. So, I’m throwing this out there.

What do you guys think? Am I over thinking this? Should I take a third option I just haven’t seen?

*point of clarification since it's come up: 4th ed had two very different classes with the name of Assassin. One was from the Insider, was bonded to the Shadowfell, teleported, had shrouds, and other shadow effects. The other was from Essentials, and from my understanding was a rogue that used poison. Mine was the Shadowfell version.
Either way, the 'conversion' has been done and we have played a couple of sessions.

Thanks in advance.
 
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Are you aware that there is a Rogue subclass called Assassin? I haven't played the Assassin in 4th edition, but this may be closer to what you're looking for than the Rogue/Bladelock multiclass you have currently. The Shadow Monk may also have the things you're looking for, though that's maybe not an option since there's already a monk in your party. In general, I don't really recommend multiclassing in 5th edition, as almost all character concepts can be made with the right combination of background, subclass, and feats.

There's also an official conversion guide available here: http://media.wizards.com/2015/downloads/dnd/DnD_Conversions_1.0.pdf, although it doesn't say anything about the Assassin explicitly. One point to think about is that it says feats from 4th edition should usually be ignored, unless it's essential for the flavor of your build.

You should also know that there's a hard cap of 20 on all stats, so you cannot spend both ASIs on dex. Concerning feats, I'd recommend Skulker for playing up to the assassin role. Warcaster and Dual Wielder are both fine feats, though I would recommend deciding on one fighting style (dual wielding or eldritch blasting) and only taking the feat that helps for that. Increasing your abilities is very important, too!

I hope this helps, and have fun with 5th edition.
 

I have to disagree with anyone suggesting the Assassin-Rogue subclass. It doesn't have the same flavor as what was in 4e though nothing fits perfect in 4e, either.

The key features of the Assassin from 4th edition were the Assassin's Shroud (a building amount of extra damage that is dealt when the Assassin attacks, regardless of whether he hits though it does less damage on a miss), Shadow Step (a lot like features existing in this edition, like the Shadow Monk's, except it teleports from being adjacent to one creature to another), Guild Training (which had two options- one which increased damage when no allies are around and one that gave temps when attacking a target with more than half-health), Shade Form (which let you conceal yourself while you weren't attacking), and an alternate to Shade Form in Black Flame Form (which gave resistance and a damage boost to melee).

With all that in mind, I'd say the closest thing to an Assassin from 4th edition in 5th edition is the Way of Shadows Monk. It has an at-will teleport, damage boosting abilities (though you don't get to keep stacking up like Shrouds), and a concealment feature.

Although, a Warlock might suffice, with the One With Shadows Invocation standing in for Shade Form and Hex standing in as Shroud. You'd have to use Misty Step to get the teleport and it wouldn't be at-will.

EDIT: I should mention that the Monk suggestion really is only good if your Assassin was melee heavy. If not, Rogue+Warlock probably looks better, so Sneak Attack and Hex can sit in as shrouds and you can grab the invocation later. Still no at-will teleport but you can at least get it as an "encounter" ability through Warlock.
 
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I believe rogue/warlock is spot on for the non essential assassin.
Maybe shadow monk would also be something to look at.
What you should not do is ölanning too hard about what class to advance levels ahead. Just increase levels as you go. 5e is balanced well enough. Your eldritch blast scales reasonably well. Your single or two weapon attacks with advantage most probably will give you sneak attack. Good invocations are devil sight to see in your magical darkness.
The only thing you need is conjuring a short sword as pact weapon and then use a normal short sword as off hand weapon to have a good damage output if that is your concern. Especially with your 18 dex. Two weapon fighting style is rather bad for a dexterity based chatacter because +2 dex gives you more.
What I would consider is assassin rather than swashbuckler. You can easily have advantage at will as warlock 3 and if you are invisible to your enemy, you can always disengage without taking opportunity attacks.
Yeah... that's it. I am sure it was a bit much...
tl dr
don't worry, you are good no matter what you do.
 

Thanks for the replies folks. I looked at the Shadow monk, but with another monk already at the table, I didn't want to double up. After seeing the monk in action, I'm glad I didn't. 2 monks wouldn't leave much for the rest of the party. ;)
 

What I would consider is assassin rather than swashbuckler.
Swashbuckler has some neat Cha synergy if you push that up.

And I agree DW is strictly worse than Dex+2.

I would get bladelock 5 for thirsting blade before pushing swash past 3 if DPR matters to you.
 
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