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I have been an AD&D 2e DM for many, many years. However, I recently decided to update to D&D 5e when I concluded that the rules in 5e — especially overall — are more to my liking. Unsurprisingly, 5e is a more polished game than AD&D 2e; this makes sense given that D&D in general has been workshopped far more by now than it had been when AD&D 2e was first created.

With that being said, in AD&D 2e, there was some really fun, crazy stuff that went down. For example, the point system for selecting non-weapon proficiencies was SO fun, beloved by all of my players and I. Because of it, players could have some of the most hilarious combinations of skills; I had a character once with the Gaming (like poker, blackjack, etc; fell under Charisma) proficiency, Astrology (reading star signs and predicting the future) proficiency, and Engineering (building cool stuff, weapons or otherwise) proficiency, and managed to combine all three in a couple situations.

In 5e, there are skill proficiencies with associated modifiers and corresponding ability scores, but there seems to be very little player choice in selecting those proficiencies. Sure, the backgrounds offer a little wiggle room as they can be customised, but nothing like the hilarious lunacy that AD&D 2e provided. Additionally, there seems not to be a way for characters to acquire additional skill proficiencies as they level up; in AD&D 2e, the non-weapon proficiency point allocation system awarded points (to be spent on new proficiencies) to characters when they levelled, and choosing new proficiencies was part of the fun of advancing as a character.

Not only that, but as a more general D&D complaint (as there's never been a good system in place for this, in my experience as a player and a DM), choosing to train in (up/boost/improve modifiers for) specific skills or abilities seems to have no place in 5e, nor in D&D in general. We had house rules that allowed players to "train" in specific skills or abilities (the 6 basic ones, plus a new d20 based ability score called "Chakra" that was analogous to mana) during pre-determined training periods, using Naruto as a model for this. In fact, we had several campaigns wherein we overhauled the spell-casting system to be Chakra based, essentially meaning that one factor determining the player's ability to cast spells at any given time was based on a fixed, decrementing mana value, and gaining new spells was based less on level and more on specifically training to learn specific spells, or "Jutsu" in those games.

TL;DR: Is there a way to give players more choice in what skills they do or do not have, both in game (as they level up) and during character creation?

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There are many ways to gain additional skill proficiencies in the rules.

If you or your players want to make a new set of proficiencies, you're free to do so using a customized background: (PHB 125)

You might want to tweak some of the features of a background so it better fits your character or the campaign setting. To customize a background, you can replace one feature with any other one, choose any two skills, and choose a total of two tool proficiencies or languages from the sample backgrounds.

The Skilled feat (PHB 170) is self-explanatory:

You gain proficiency in any combination of three skills or tools of your choice.

As a DM, you can let your players get training in skills in order to gain proficiency: (DMG 231)

A character might be offered special training in lieu of a financial reward. This kind of training isn't widely available and thus is highly desirable ... Possible training benefits include ...The character gains proficiency in a skill.

However, consider that this bonus is in the same list as gaining an extra feat, so it's not something to be done lightly.

Finally, both the rogue and the bard have ways of boosting their skills. Rogues can double their proficiency bonus for a handful of skills through the Expertise feature (PHB 96) and bards get half of their proficiency bonus to any check that doesn't include their proficiency bonus (PHB 54).

You might be interested in the Background Proficiency variant rule

DMG 264 has the "Background Proficiency" variant rule, which seems to hew pretty closely to the mechanics you desire:

With this variant rule, characters don't have skill or tool proficiencies. Anything that would grant the character a skill or tool proficiency provides no benefit. Instead, a character can add his or her proficiency bonus to any ability check to which the character's prior training and experience (reflected in the character's background) reasonably applies. The DM is the ultimate judge of whether the character's background applies.

You don't need specific rules to make crazy situations

Why did the designers get rid of the skill point system in the first place? Mike Mearls said:

We unified the progression for skills and weapons under one set of rules. That removed a lot of complexity and allowed us to include skills in the simplest version of the game without adding a lot of rules overhead.

Therefore, instead of depending on an arguably unwieldy and complicated set of rules for skills, you can use the simplified framework of 5e to create the kinds of specific "proficiencies" that you describe in your question.

More specifically, you can let your players add their proficiency bonus to specific kinds of checks, or even give advantage for more significant bonuses. If your character is an expert in astrology, maybe let them add their proficiency bonus to Arcana, Nature, or Religion checks that involve the stars. Examples of this kind of bonus exist throughout the system: for instance, the Belt of Dwarvenkind gives advantage on persuasion checks against dwarves.

Indeed, such cases are what the advantage mechanic was made for: the DM giving quick bonuses in response to favorable situations. You might find that this goes a lot smoother than a skill point based system. As a player, I've found that DM bonuses like this are not only balanced (because they're highly situational), but also a lot easier to keep track of than, say, 3.5's super complicated skill system.

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    \$\begingroup\$ I suggest that you also mention the feat that adds skill proficiency, and the Rogue and Bard skill proficiency increases with levels. \$\endgroup\$ – KorvinStarmast Jun 2 '17 at 12:45
  • \$\begingroup\$ This could also mention downtime training to get tool and language proficiency. \$\endgroup\$ – Derek Stucki Jun 2 '17 at 15:51
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1) You actually can train up skills in 5e! You don't need levels or experience, you need cash and a trainer. Also a LOT of downtime, even coming from AD&D, but it doesn't have be spent all at once. You can read more about it in the DMG.

2) You can totally replace 5e's skill list and/or distribution method with AD&D's. I have friends who have done this and it works fine. 5e's skill system is essentially a return to proficiency v.s. non-proficiency instead of ranks for skills, and if you like the old list better you can certainly use it.

If you use the old list, you'll need to replace the written skill checks in modules, if you use them, but there are a lot of equivalencies and regardless it sounds like you are used to adjudicating DCs and applicable skills of the cuff anyways.

If you use the old distribution method, you'll need to make tables for the new classes. They based theirs off the balance of the older AD&D classes, but you basically just need to decide what level of skill proliferation fits your campaign best.

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  • \$\begingroup\$ you need cash and a trainer and time - a lot of it. [...] The training lasts for 250 days [...] (PHB. 187). It's rather prohibitive in the context of a normal campaign. \$\endgroup\$ – JBC Jun 2 '17 at 13:45
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In my game, during character building we would take into account a characters backstory to help determine proficiency. For example, say we had a character that spent a lot of time in their past as a student of history. It would make sense for them to be proficient in History, even if none of the options afforded to them by their class or background say they can. It makes more sense that way than saying, "Sorry you can't be proficient in history because the book says no." I feel like that gives more life to the characters. Now, I may make it a trade off for something else that maybe doesn't make as much sense for their character. But it depends. As long as it doesn't break the game I see no harm in it.

Same for gaining proficiency as a skill in game. If a player wants to train to become proficient in something I would allow it. Depending on what it is depends on what task they would have to do to become proficient. The way I look at it, as long as it makes sense its fine. But it will take work, especially if it isn't something that type of character would have come naturally based on how their character is played or their characters story. So maybe a warlock who wants to be proficient in animal handling. Their characters story doesn't make that make sense. But if they spend enough time with animals, and they work at taming or domesticating them, through some hard work they can earn it. Make sure it takes time and is not easy, so it is more rewarding.

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  • \$\begingroup\$ If the background suggest the character should be proficient in History, then the player should have selected it in lieu of something else in the Background they picked. The rules allow substitution. The DMG has rules for training, and the PHB has a feat for it. \$\endgroup\$ – T.J.L. Jun 2 '17 at 16:21

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