Quote Originally Posted by Greywander View Post
The only reason you would need to slot players or monsters into categories is to give one category or character a bonus or penalty against another category. Which I suppose is functional (Age of Empires does this, e.g. with spears doing bonus damage to cavalry), but it's kind of boring. So instead of putting characters into limited categories, I think it makes more sense to give them sets of abilities. One ability makes you good at one thing, and another ability is able to counter it, though not necessarily directly. For example, the ability to fly is a huge benefit when all your enemies are melee attackers, but a ranged attacker more or less negates that benefit entirely, and not because ranged attacks have any special interaction with flying creatures (though in some systems they do).
The point though is that in the pursuit of those categories you remove very iconic things from the game on both sides. For example, saying that you can't fly and be good at ranged or melee means no druids, no vampires, no dragons... It's fine for a different game but not D&D.

Quote Originally Posted by Greywander View Post
It depends what you mean by a "heavily specialized build". A longbow fighter built around maximizing their ranged damage is heavily specialized, but damage is broadly applicable. A sorcerer who only takes fire spells is also heavily specialized, but in a different way.
Fire sorcerer is much closer to what I was talking about than longbow fighter. A longbow fighter is not heavily specialized; in situations where the bow is not useful, they can grab a scimitar and shield just fine and still be above baseline effectiveness. Extra Attack, Action Surge, their proficiencies and Dex all still apply.

Quote Originally Posted by Greywander View Post
Also, the math of the d20 mechanic means that it's actually more effective to stack your bonuses on one type of roll. For example, if an enemy hits you on an 11 that's a 50% chance to be hit. If you gain +1 AC then now they only hit on a 12 or better, which is a 45% chance to hit. That's a 10% reduction in the number of hits taken. But if an enemy needs a 19 to hit you (10% chance), and you gain +1 AC, now they can only hit on a 20 (5% chance). That's a 50% reduction in the number of hits taken, from the same +1 bonus. The same math applies to anything that uses a d20 roll. For example, you're better off maximizing one or two saving throws instead of trying to balance them all. So the math behind the d20 roll really does reward specilization.
That kind of specialization is dependent on the availability of said bonuses. Sure in 3.5 there's a smorgasbord you can stack onto one check, but not so much in 5e.