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I am trying to get my head around understanding the benefit of multi-classing over gestalting.

When multi-classing, each class is leveled up separately which hurts the overall progression of your character.

Multiclass example: A character that multi-classed into: Warlock 3 / Rogue 2 would have an ECL of 5 because it counts as 2 separate classes.

So why not gestalt if it is allowed by the house that way both classes level at the same time?

Gestalt example: A character that gestalted into: Warlock//Rogue level 5 would have ECL of 5 because it counts as one class.

Bottomline: Unless I've understood something wrong, isn't gestalting superior in every way when it comes to a character's class progression? What are the advantages/disadvantages of choosing gestalt over multi-class and vice versa?

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Gestalt isn't a choice, it's a game variant.

That's very important to understand when asking why you don't just do it: because it's not generally assumed that it's a valid option.

The game doesn't necessarily say you can take feats and classes from books like Complete Arcane, but it's understood in the community that unless the campaign coordinator notes otherwise, warlock is a valid class to play in D&D 3.5.

Unearthed Arcana, the book that introduces gestalt characters, is more explicit about the role of the rule:

The gestalt character variant is particularly effective if you have three or fewer players in your D&D group, or if your players enjoy multiclassing and want characters with truly prodigious powers. This variant works only if every PC in the campaign uses it, and it results in complicated characters who may overwhelm newer D&D players with an abundance of options.

That second sentence is very important: It's not a choice, it's a fact of the characters using it and the campaign they're in.

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    \$\begingroup\$ It's also worth noting that multiclassing is (unless specified otherwise) still an option in gestalt campaigns, and is still usually a good idea. \$\endgroup\$ – Miniman Mar 11 at 5:34
  • \$\begingroup\$ @miniman especially because you are multiclassing into another gestalt combo. Like a Rogue/Warrior multiclassing into Wizard/Cleric. \$\endgroup\$ – Mindwin Mar 11 at 14:35
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Players don’t have a choice to use gestalt or not

Gestalt is something the DM chooses, as the rules for the game. So as a player, you’re either playing in a gestalt game, and thus must use those rules, or you are playing in a non-gestalt game, and cannot use those rules. Aside from looking for a gestalt game to play in, the player has no ability to choose to use gestalt.

This is consistent with Unearthed Arcana as a whole. Other supplements, like Complete Arcane or Tome of Battle, provide additional rules that are simply added on to the existing game. If the DM says those books are in-play, you can use the options in them; those options are just supposed to fit into the game without a problem. Unearthed Arcana is different—the DM can’t just say it’s “in play,” that doesn’t make any sense. That’s because rather than add-on rules, Unearthed Arcana offers a bunch of variant rules—they change how the game is played in fundamental ways. The DM has to decide which variants they are or are not using. Many variants simply can’t be used at the same time as others.

Anyway yes, gestalt characters are stronger than non-gestalt characters. It’s far superior to regular multiclassing. That’s an intended and understood aspect of the variant—and Unearthed Arcana goes out of its way to warn DMs about that. A DM has to make challenges harder for gestalt characters than they would for non-gestalt characters of the same level, because a gestalt character has more abilities and features than a non-gestalt one. In one game I’m playing in, our characters are 6th level, but have four “layers” of gestalt (that is, two more after the usual second one for gestalt)—we are routinely fighting challenges intended for characters in the mid-teens, because even though we’re still 6th level, all those features make our characters fairly powerful.

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Long story short: Gestalt is an optional rule to increase the power of the players/certain classes. If a DM allows gestalting, it's kinda counterproductive not to, but unless this option is specified, it is off the table.

So far, I've seen two major implementations for gestalting:

  • Allowing all players to gestalt in order to create a high-power game overall
  • Allowing low tier classes to gestalt with each other to level the class balance somewhat, since Monk/Fighter gestalt just might be close enough to a singleclassed Wizard (it's usually not, but free extra stuff makes the power gap more tolerable)

Meanwhile, Multiclassing is always available unless specified otherwise, so if you want to make some sort of a Wizard/Barbarian hybrid, that's usually your option to go.

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    \$\begingroup\$ On that last line, don't forget the make sure that you DM is ignoring those rules that give you XP penalties for multiclassing. \$\endgroup\$ – J. Mini Mar 11 at 13:30
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    \$\begingroup\$ Yeah, that rule is terribad (multicclassing comes with its own setbacks as-is, and XP penalties for ir are completely unnecessary) \$\endgroup\$ – Baka-Mastermind Mar 11 at 14:29
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    \$\begingroup\$ @j.mini that's the first one that flies off the window. Just remember to give the half-elf some love because supposedly it was one of his racials. \$\endgroup\$ – Mindwin Mar 11 at 14:36
  • \$\begingroup\$ "Monk/Fighter gestalt just might be close enough to a singleclassed Wizard (it's usually not" That depends on the current character levels and the setting/play-style. At low levels, especially if you can't rest often, a well made monk/fighter would make the wizard player feel nearly useless. Most wizard players would not start feeling very useful in combat-heavy games until they got third level spells. And a well designed monk/fighter that receives buffs will be dealing consistent damage every round even later as well. You have a good point, I just think it's overstated. \$\endgroup\$ – Aaron Mar 11 at 19:38
  • \$\begingroup\$ Well. yeah. all talks about class balance are based on an even playing field, with equal player skill and somewhat standard fight dynamics. A complete noob Druid will likely feel inadequate next to a powergamer Soulknife (or hell, even a chicken-flinging basketweaving powerplayer Commoner), and a game stacked against one type of characters also shifts the scale. If a DM exclusively showers a Commoner noob in epic artifacts and stacks odds against the rest of the party, the noob will feel more powerful than the rest of the table too. Can't account for everything \$\endgroup\$ – Baka-Mastermind Mar 14 at 4:49
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Why gestalting is better than multi-classing:

Gestalt rules will vary from table to table but the core concept is that you take multiple class level per character level as opposed to multi-classing, in which you take one (different) class level per character level. The reasons why this makes gestalting better than multi-classing for your character chassis are manifold:

  • Spellcasting progression - Most spellcasters will try to avoid multi-classing because advancing another class will cause you to delay your spellcasting progression. Gestalting allows you to level your spellcasting class at the same time you progress another class, resulting in no delays to reaching higher-level spells.
  • Saving throws - Some classes have powerful abilities in return for weak saves (Barbarian Will saves, Wizard Fortitude saves). Depending on your gestalting rules, you can compensate for those weak saves either by gestalting a class with high base saving throws (Monk) or a class that has bonuses to saving throws (Paladin). Imagine a Barbarian with a Monk's +12/+12/+12 saving throws.
  • Base attack bonus - Like with saving throws, you can compensate for a class's poor base attack progression by gestalting a class with a better base attack bonus, like Wizard+Fighter.

There are more reasons but at the end of the day, gestalting is better than multi-classing because you are adding abilities on top of your existing class progression, not taking a side trip and ge-stalling your original journey. Think two fruits for the price of one versus buying an apple and an orange. This is why gestalting is a campaign variant rather than a character option. If multi-classing is allowed (people forget that this is also an optional rule), you can choose not to multi-class. But gestalting is decided as part of the campaign setting.

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  • \$\begingroup\$ What about multiclassing is an optional rule? Everything I can find in the Player's Handbook is pretty nonchalant about how multiclassing is a thing you are able to do. Are you thinking of another edition, perhaps? \$\endgroup\$ – Powerdork Mar 28 at 2:22

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