Skill Based Half-Elf

[TheTacoBandit]

I enjoy role playing and have done several evil characters but now I want to do a nicer character. I was thinking about playing a skill based Half Elf Female because it would be funny and enjoyable and not be a absolute retardation to the group. I want to have high Charisma and Dex over Strength and Con because I already have a tanky Half-Orc. I was thinking of Bard but then the idea of multi-classing as an Arcane Trickster came to me since I would have high CHA and DEX. Also my group love homebrew and we often go over Level 20 on the grounds that Gods have supercharged us or some BS. So that's an option. Assuming though that I will only be going to Level 20 what would be a recommended build for a Charismatic Skill Based Half Elf Female?

[Naanomi]

Either Lore Bard general skilled type, or assassin rogue 'master of disguise'?

[Giant2005]

If you want to be skill-based, then shoot for all 18.

There are two ways to do that by level 7:
1. The Half-Elf Way: Start as a level 1 Rogue, multi into a Lore Bard and take 4 levels of it (Take the Skilled feat), Take a level of Cleric (Knowledge Domain), take a level of Ranger.
2. The Variant Human way: Start as a level 1 Rogue and take the skilled feat as your human trait, take 3 levels of Lore Bard, a level of Cleric (Knowledge) and 2 levels of Warlock (And take the Beguiling Influence Invocation)

It sounds like you want to be a Half-Elf, so obviously option 1 is probably going to be more useful to you but if you are only choosing Half-Elf due to the extra skill it gets, then it isn't really necessary and the Human option is back on the table.
Each option has their own merits:
Option 1: Has the potential to reach level 9 Bard spells if you are so inclined and requires only 3 levels of multiclassing. However if you really want to be a skill-monkey, you are probably going to want to end up with a minimum of 6 levels of Rogue for the extra set of Exprtise skills.
Option 2: You get an extra ASI to play with at level 8 due to not yet having 4 levels of Bard. 2 levels of Warlock is far more useful than 1 level of Ranger but it can never attain level 9 spells but that isn't an issue if you intend to take more Rogue levels for more Expetise.

[ImSAMazing]

I enjoy role playing and have done several evil characters but now I want to do a nicer character. I was thinking about playing a skill based Half Elf Female because it would be funny and enjoyable and not be a absolute retardation to the group. I want to have high Charisma and Dex over Strength and Con because I already have a tanky Half-Orc. I was thinking of Bard but then the idea of multi-classing as an Arcane Trickster came to me since I would have high CHA and DEX. Also my group love homebrew and we often go over Level 20 on the grounds that Gods have supercharged us or some BS. So that's an option. Assuming though that I will only be going to Level 20 what would be a recommended build for a Charismatic Skill Based Half Elf Female?

If you want to be a Arcane Trickster/Skillmonkey(Bard), go like this: first take 6 levels in Bard so you get Jack of all Trades, 2 times expertise and some useful bard spells. Then take 6 levels in knowledge domain(Cleric) so you can use Channel Divinity for free skill of choice. Then take 6 levels in Rogue. Then choose if you want to continue in Bard, Rogue or Cleric.

[djreynolds]

I have "5th character sheet" app. I made a half elf rouge, bard ranger cleric and he got all the skills. I went 8 rouge, 1 ranger,10 bard , 1 cleric. And all the skills were green. Thieves tools don't show up but you can expertise with it. You could just 6 rouge and more ranger for the archery. I think I went custom, urchin gives tools

[Ashrym]

Just starting half elf rogue and taking the skilled feat at some point covers most of what you want. That's 11 skill proficiencies to really take advantage of reliable talent later.

You can squeeze in more but that messes up ASI's and progression. If you do want more go for 3 bard levels for lore and that will add 4 more skill proficiencies and 2 more with expertise, plus you can add in the enhance ability spell and jack-of-all-trades covers the other few skills. That lets you keep the 17th level rogue archetype ability too, and you still end up with 4 ASI's after the skilled feat.

Arcane trickster 17 / bard 3 will also still open up 4th-level spells. It's pretty solid for skills but 3 levels of higher level ability delay can be annoying.