3.5E to 5E PC conversion

[dpm_dj]

Good morning,

In a couple of months my party will continue a long pirate campaign made with 3.5E PC.
Our DM asked us to convert them into 5E characters.

We were 12th level but for history reasons we went back to 3rd level.

My character almost literally used the build of the daring outlaw (3.5E Optimized Character Build) at Dandwiki (no Tome of Battle).

IYO what do you recommend, considering that I am quite free on manuals (Forgotten Realms setting) and that the idea is to fully recover the taste of the PG with mechanics as similar as possible? Use of talents and multiclass absolutely possible.

Thanks in advance!

[Amnestic]

From a quick look at the build online (assuming it's this one) it looks like the sort of thing which can be replicated by just taking the Swashbuckler subclass for rogue.

The build has minor spellcasting too from what it looks like, so you could splash into bard or warlock for that to keep the Cha synergy.

[Kane0]

Looks a Rogue with some Fighter and/or maybe Ranger thrown in to me. The basic parts appear to be:

- Mixing swashbuckler and rogue for a full SA progression and better than average BAB. In 5e Swashbuckler is by default a variety of Rogue and Prof Bonus replaced BAB so basically everyone shares a similar to-hit
- Maximising full attack + movement. Everyone in 5e gets that, and Rogues can double their movement or run away without AoOs at level 2 without sacrificing their attacks.
- Crit-fishing. Champion fighter (chosen at fighter 3) and the Elven Accuracy feat is good for this, plus maybe one of the piercer/slasher/crusher feats.
- Getting as many attacks as you can. Sneak attack only works once per turn but Extra Attack from 5 levels of most warrior classes is great for making sure you land it, plus getting hasted or action surge to ready an extra attack for when it's not your turn lets you double-dip sneak attacks. Swashbuckler Rogues do get some great incentives to dual wield however, and there is the fighting style and feat to support it further.

If you're back to level 3 just make a Swashbuckler Rogue, then as you get familiar with the system and level back up consider if you want to take 2-5 levels in Fighter or Ranger. Both have their benefits and sync nicely with Rogue but there are tradeoffs.

[dpm_dj]

Thank you guys.
Errata: we start 5th level.
This campaign will go on for a very long time, so it will end probably at 12/14th.

My PC is the typical wise man, lieutenant of an also clever and charismatic general (bard/swashbuckler and also king of the pirates in this case, after this two-year-long campaign), in a party/family (all human brothers or cousins) made of a druid, a cleric and a necromancer (yes, you know, pirates... Evil but at different stages for each one).
The point is that I'm really nothing special on the battlefiled, but my main ability is to work offstage (like Littlefinger of GoT, but not disgusting like him).

That said, what could it be a possible build for a character like this?
Thanks in advance.

[Abracadangit]

Thank you guys.
Errata: we start 5th level.
This campaign will go on for a very long time, so it will end probably at 12/14th.

My PC is the typical wise man, lieutenant of an also clever and charismatic general (bard/swashbuckler and also king of the pirates in this case, after this two-year-long campaign), in a party/family (all human brothers or cousins) made of a druid, a cleric and a necromancer (yes, you know, pirates... Evil but at different stages for each one).
The point is that I'm really nothing special on the battlefiled, but my main ability is to work offstage (like Littlefinger of GoT, but not disgusting like him).

That said, what could it be a possible build for a character like this?
Thanks in advance.

This is really gonna cook your noodle: the Swashbuckler subclass HAS an ability that lets you charm people based off of your winsome personality, as opposed to magic. You could easily fluff that as a Littlefinger-esque flair for politicking and psychology.

So rogue/swashbuckler is gonna be your primary level sink, but you could also buy a bard dip for your bardic abilities, maybe 3 so you get a bard subclass ability.

For your background, instead of bonus languages, you could go tool prof. in navigator's tools and sea vehicles, and there's your pirate.