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As a character levels up in Pathfinder 2e, at every odd numbered level, they can increase their level of training in one skill. From Untrained to Trained, or, starting at level 3, from Trained to Expert, at level 7 from Expert to Master, and starting at level 15, from Master to Legendary proficiency.

For many of characters, what this means is that they will increase two skills to Expert at 3 and 5, increase those same two skills from Expert to Master and 7 and 9, and can then increase a third skill to Expert and then Master at 11 and 13, and then at 15, 17, and 19, increase those three Mastered skills to Legendary.

The Skill Training feat allows a player to add additional skills at the baseline level of Trained (as does allocating an ability boost to Intelligence), and Rogues gain a skill increase at every level (effectively doubling the number of Expert/Master/Legendary skills). But there are no other General Feat based options for increasing a skill beyond the level of Trained. That means unless you're playing a Rogue, you'll never have more than three skills (and no more than two below 13th level) at the maximum bonus attainable at a given level.

Unless.... Are there other ways to increase the proficiency rank of skills?

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    \$\begingroup\$ It’s worth noting that the difference between Trained and Legendary is much smaller than the difference between Untrained and Trained. The main purpose of Expert/Master/Legendary is about which feats you qualify for. \$\endgroup\$
    – KRyan
    Nov 4, 2022 at 4:35
  • \$\begingroup\$ @KRyan, many high level hazards and haunts can only be disabled with expert/master proficiency \$\endgroup\$
    – András
    Nov 6, 2022 at 10:34
  • \$\begingroup\$ Each level of proficiency is worth +2. Yes that’s smaller than the gap from untrained to trained, but in a system with degrees of success, every +1 is a huge increase in the utility of a given skill. \$\endgroup\$
    – LessPop_MoreFizz
    Nov 6, 2022 at 13:44

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Other Classes

You've mentioned Rogue as getting additional skill increases and that they're able to use those to get 6 legendary skills by level 20, but Investigators also have that same ability to get a skill increase each level.

Also worth mentioning is that the Construct Innovation of the Inventor can gain legendary proficiency in Intimidation, Stealth, Survival, and any Intelligence- or Charisma-based skills of the character's choice through the Miracle Gears revolutionary modification. This isn't included below because only the companion gains the proficiency.

Specific Skills

Quite a few options exist to grant legendary proficiency in specific skills, often increasing proficiency to legendary at 15th level, including the following:

Treated as Higher Proficiency

Similarly, there are a few options that allow characters to act as though they have a higher skill rank for some particular purpose. I'll include Perception in these even though it technically isn't a skill:

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    \$\begingroup\$ It may be worth adding the Skill Mastery rogue/investigator archetype feat. It doesn't give you Legendary, but it can give you Master in more skills and generally keep more skills "at-level" since that seems to be half of OP's intent. \$\endgroup\$
    – Ifusaso
    Nov 4, 2022 at 18:59

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