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I was reading through the Scout's Survivalist feature and noted that it is a manner by which a character can both gain skill proficiency plus Expertise in one shot. This got me wondering how many skills I could potentially get Expertise in for a single character. There have been several questions inquiring on maximizing a character's skill and tool proficiencies, but I haven't been able to identify any question discussing maximizing a character's Expertise.

For the purpose of this question, assume the following:

  • Assume the character is allowed 20 levels.
  • Only the character in question should be considered (i.e. no outside help).
  • No epic boons.
  • Any skill, feature, or item which allows the character to double their proficiency bonus for a skill is valid, it does not need to be called 'Expertise' to qualify.
  • Use of any skill, feature, or item needs to have a tangible benefit. For example, if you need to be proficient in the skill in order to get the benefit of double the proficiency bonus, then that proficiency must be gained somehow to satisfy the pre-req. This avoids issues of having more Expertise than skill proficiencies raised by this question.
  • Always-on is preferable to a short-term Expertise (such as what's granted by Skill Empowerment).
  • Wish may be used solely within the confines of duplicating a spell.
  • Multiclassing is permissible.
  • Variant humans and feats are permissible.
  • Any published background is permissible (i.e. no custom backgrounds).
  • Magic items are permissible of any rarity except Artifact.
  • No use of downtime to gain skill proficiencies.

I will consider the best to answer to be whichever one is able to come closest to gaining Expertise in the 18 skill proficiencies in the game. In the event that multiple answers can achieve this, then Tool proficiencies will be considered.

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    \$\begingroup\$ Related: rpg.stackexchange.com/questions/120807/… \$\endgroup\$ – Thomas Markov Apr 21 at 15:37
  • \$\begingroup\$ How big a loophole would downtime to gain skills be? It seems to me at least interesting to consider, as a side note for answers to mention. (Although I forget if there's any standard rule for gaining skill proficiencies that way, as opposed to languages or tool proficiencies.) \$\endgroup\$ – Peter Cordes Apr 22 at 8:05
  • \$\begingroup\$ @PeterCordes I think it'd be pretty big. If it were allowed, then it can effectively be equal to the epic boon of Skill Proficiency. But assuming you wanted to allow it then you'd have to caveat a bunch of rules for it (i.e. how much gold and downtime is available for the training and at what level), which is beyond the scope of what I'm shooting for here. I'm aiming to have something that's likely to be permitted at most any table. \$\endgroup\$ – Pyrotechnical Apr 22 at 13:27
  • \$\begingroup\$ Ok right, just the way you phrased it got me wondering if there was a rule for it, but you wanted something that would work without downtime for a character in a hurry. But no, there isn't for skills. But PHB and Xanathar's do have rules for learning tool-proficiency and languages in downtime. Anyway, what I was really wondering was impact on this question, not on game-play generally, and tool is fine! (Overall impact would be huge if time+gold could get anyone a key skill like perception or stealth.) \$\endgroup\$ – Peter Cordes Apr 22 at 20:32
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You can get expertise in fourteen skills (plus one from skill empowerment), and nine tools

Classes: Rogue (Scout) 6, Bard (Lore) 10, Cleric (Knowledge) 1, Fighter (Rune Knight) 3

Use the Sailor background to get proficiency in Athletics, Perception, Navigator's Tools, and Vehicles (Water). Be a Half-Elf so you can pick up another 2 proficiencies (Acrobatics and Animal Handling) and you qualify for the Prodigy racial feat from Xanathar's.

For our 6 levels in Rogue, pick Stealth, Sleight of Hand, Persuasion, and Performance right off the bat and expertise in Acrobatics, Stealth, Sleight of Hand, and Perception. We also get proficiency in Thieves' Tools. At level 3 we choose Scout, which gives us proficiency and expertise in Nature and Survival. When you hit a feat, take Prodigy and select a tool (let's go with Woodcarver's Tools) and Deception, making that expertise at the same time. We leave Rogue with 11 skill proficiencies, 7 of which are expertise, and 4 tool proficiencies.

Our 10 levels in bard we choose Insight and a musical instrument (Pan Flute) when we join, and choose College of Lore at the same time we choose expertise in Performance and Persuasion. We also choose 3 new skill proficiencies, Intimidation, Investigation, and Religion. At our first feat in Bard we take Skill Expert, taking Medicine and making it expertise. Our second feat in bard we take Skilled, and choose 3 tool proficiencies (Potter's Tools, Weaver's Tools, Jeweler's Tools). At level 10 we take expertise in Insight and Intimidation. We leave Rogue and Bard with 16 skill proficiencies, 12 of which are expertise, and 8 tool proficiencies.

We take 1 level in Knowledge Domain Cleric, gaining Arcana and History, both with expertise. We leave Rogue, Bard, and Cleric with 18 skill proficiencies, 14 of which are expertise, and 8 tool proficiencies.

For our last 3 levels, we take Fighter, choosing Rune Knight as our Martial Archetype. At level 3 we get proficiency in Smith's Tools, and with Fire Rune you double your proficiency with every ability check using a tool (granting expertise to all your tools). We leave Rogue, Bard, Cleric, and Fighter with 18 skill proficiencies, 14 of which are expertise, and 9 tool proficiencies, all of which are expertise.

Additionally, with our Bard spellcasting, we can cast Skill Empowerment to get expertise in one of the other skills that don't have it.

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  • \$\begingroup\$ I'm just reviewing the question and I think tool expertise might be out of scope - question i is on 'number of skills a character can gain expertise in' \$\endgroup\$ – Lovell Apr 21 at 21:53
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    \$\begingroup\$ "In the event that multiple answers can achieve this, then Tool proficiencies will be considered." That was the last sentence in the question, so it's not entirely out of scope. \$\endgroup\$ – RallozarX Apr 21 at 23:18
  • \$\begingroup\$ I see what you were talking in the comments. This takes Lovell's build as a base, but then expands on it. \$\endgroup\$ – Egor Hans Apr 23 at 7:11
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Fifteen

With a level 17 Rogue/Cleric/Bard

Race: Half-Elf, so you can pick up another 2 proficiencies and you qualify for the Prodigy racial feat from Xanathar's

Any background that gives us two skill proficiencies

Feats:

  • Prodigy (XGE) + 1 expertise in any skill and 1 additional proficiency
  • Skill Expert (TCE) + 1 expertise in any skill, 1 additional proficiency and proficiency in thieves' tools

Classes:

6 levels in Rogue (scout)

This is our base class so we can pick up another four proficiencies

Don't take proficiency with thieve's tools, because we can get that from prodigy and then gain expertise on it at level 6.

+4 expertises from base class, + Nature & Survival from Scout (proficiency and expertise)

1 level in Cleric (knowledge domain)

+2 expertises, with underlying proficiency, from one of arcana, history, nature or religion

10 levels in Bard (College of Lore)

Another 4 expertises, and another three proficiencies from the subclass at level three. Plus we can cast Skill Empowerment to get another expertise.

That's 15 sources of expertise and 17 proficiencies onto which we can place them.

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  • \$\begingroup\$ Let us continue this discussion in chat. \$\endgroup\$ – Lovell Apr 21 at 16:24
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    \$\begingroup\$ I've worked out an answer that is so similar to this, I'll just suggest an edit instead. It's your answer but with expertise in 9 tools as well. Take a background with 2 tools like Sailor, then take Skilled later on to get 3 tools. For the last 3 levels take Fighter (Rune Knight) and the Fire Rune doubles proficiency with tools. You should have 9 tool proficiencies (2 from background, 1 from rogue, 1 from prodigy, 1 from bard, 3 from skilled, and 1 from rune knight). It doesn't take anything away from your answer, just gives a little more. \$\endgroup\$ – RallozarX Apr 21 at 16:45
  • \$\begingroup\$ @RallozarX That sounds like a totally different approach, please post a new answer. \$\endgroup\$ – Thomas Markov Apr 21 at 16:47
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    \$\begingroup\$ @Thomas Markov Could you tell me how it's a different approach? I'll post a new answer, but I don't see why. \$\endgroup\$ – RallozarX Apr 21 at 16:54
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    \$\begingroup\$ @Pyrotechnical Ive reproduced this build on dndbeyond using only skill proficiencies. \$\endgroup\$ – Thomas Markov Apr 21 at 17:08

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