Converting Player Characters from past editions to Dungeons & Dragons Fifth Edition

• Race/subspecies: This should stay the same or use the closest equivalent. For example, a Grugach (Wild Elf) can use the Wood/Sylvan Elf with the Outlander background. For unusual races, fan-written conversions are often available online.
• Occupational class, experience level: These should stay the same or go to the closest equivalent. Archetypes replace AD&D2 kits and D&D3.x prestige classes. Multiclassing should be relatively rare in larger, well-rounded parties, but use the D&D5e rules if necessary.
• Backgrounds, inspiration: Aspects from the D20/FATE version of the “Vanished Lands” should be fine here. Backgrounds can be “tagged” for advantage on a roll (or +1d6 after one), and the Game Master can invoke them and reward an inspiration point.
• Ability scores: These should stay the same, accounting for level adjustments. For new P.C.s, roll 4d6 for each attribute, re-rolling ones and dropping the lowest; reorder as desired.
• Proficiencies/skills, feats: These should also go to the closest, but note that there are fewer feats in D&D5e. See also Leadership below.
• Spells: Rather than try to convert spell by spell, use the D&D5e number of spells available by class and level, and try to pick most of your grimoire from this edition. Other spells will be approved on a case-by-case basis.

Magic items

Characters in D&D3.x, Pathfinder, and D&D4e tend to have more magic than those from previous or later rules sets. When converting higher-level P.C.s into D&D5e, you’re limited to total enchantment slots equal to level. Set aside any extra items as not being currently carried.

Thus, a fifth-level character could have a +1 weapon, +2 armor, and +2 in miscellaneous magic. When updating items, the frequency/cost in the D&D5e Dungeon Master’s Guide is preferred to past editions, but certain items will be assessed on a case-by-case basis.

Leadership

Although there isn’t yet an official mechanic for followers in D&D5e, higher-level characters should consider taking the Leadership feat as described in D20/Pathfinder.

Characters at “name level” (Lvl. 10) and above should consider founding a stronghold and/or organization, joining one, or attracting and developing a personal cohort. While not every Cleric has to build a temple, nor every Fighter must build a castle, a Rogue join a guild, or a Wizard take apprentices, P.C.s should reach positions of authority as they become experienced.

Languages

Currently, characters get languages from races and backgrounds in D&D5e. However, the only way for them to gain more is to get the Linguist feat, which increases Int by 1 and provides 3 languages.

Characters are allowed to get a new language every 3 levels in addition to those above. The total number of languages a character can learn (in addition to his or her native language and/or the regional Common tongue) is their Int bonus x2. This would allow characters to get new languages about every 15 sessions without replacing the feat.

Consult this list for languages.

In addition, P.C.s who choose not to take a new language every third level could take a +2 specialization in an existing skill — such as History: Heraldry or Survival: Plains — or proficiency in a cross-class skill every 6 levels.