Personally, I’d say you’re about done with fighter and swashbuckler

I try to avoid taking more than 3 levels of swashbuckler (insightful strike is its best feature) or 2 levels of fighter (a feat per level is OK; a feat every other level is pretty weak). I’d say it’s probably a good time to leave those classes behind.

The exception is if you take, e.g. Daring Outlaw (see below) to improve these classes. The Zhentarim Soldier ACF can also do wonders for the fighter class (up to 9th level anyway) if you have the Charisma and Intimidate ranks for it.

Classes

The best answer is warblade (but you don’t have that allowed)

Just for the sake of anyone else reading this, the warblade (Tome of Battle) is perfect here: he’s flashy, highly-skilled, and makes good use of Intelligence (and he gets 4+Int skills). White Raven makes him an excellent battlefield leader.

You already have Int to damage: factotum adds Int to (almost) everything else

(I just noticed you don’t have factotum listed either; that’s a real shame. Again, leaving this here for future users who do)

Factotum (Dungeonscape) sounds really perfect for your character here. They do gain a few spells (and some Supernatural abilities), though there are homebrew variants that can remove them. More importantly, the factotum’s whole schtick is “I add Intelligence to everything.” Like all Strength and Dexterity skill and ability checks (e.g. Athletics, Acrobatics, Stealth, Initiative) at level 3. In fact, the only notable thing that factota don’t add Intelligence to is damage: that you already have from swashbuckler’s insightful strike.

And a factotum is always the man with the plan, even if he’s actually just making it all up as he goes along. Seems like a pretty good guy to follow.

See this question for more information on using the factotum class well.

You may already qualify for chameleon, and it’s pretty good

You may qualify for the chameleon prestige class (Heroes of Destiny or here) based on Able Learner (depends on whether or not you’ve been putting points in the skills you need). While the best feature of chameleon is their spellcasting options, you don’t need to use them. Two levels of chameleon gets you the wonderful “floating feat,” a feat you can change every day. A third level can get you some sneak attack damage, which is useful (see below re: Daring Outlaw).

If you qualify for that, you might also make a good master of masks

This prestige class (Complete Scoundrel or here) isn’t very good and is probably way too specific for you: you want to be a leader of men, not hiding behind constantly-changing masks. But if you take just one level (i.e. only get one mask), and choose the gladiator mask, you get to be Maximus. You become proficient in every weapon ever, which is pretty awesome, and we all know how Maximus leaves everyone entertained.

Dread commando is fitting, but not very strong

The dread commando prestige class (Heroes of Battle or here) is full-BAB and gets sudden strike, which is the weak version of sneak attack (and stacks with sneak attack for qualifying). Requires Dodge and Mobility, which is a shame since they’re pretty weak and you should have ranks in Tumble to avoid AoOs anyway. Mobility, at least, can be gotten as an armor special ability (and the rules do allow you to qualify using items, but make sure DM allows it), but it’s quite expensive for your level.

Note that there are several feats (Midnight Dodge from Magic of Incarnum, Expeditious Dodge from Races of the Wild, Desert Wind Dodge from Tome of Battle) that count as Dodge and are better. Still not good, but better. Worth considering.

Anyway, dread commandos are skilled fighters, and the bonus damage is good for a finesse build, and you get some team-based bonuses. So fitting. But it’s a weak form of bonus damage and the team bonuses are pretty small, so not very good.

A little bit of bard could work

Bards require ranks in Perform, but unless you use their spells they don’t actually need Charisma. Just one level for inspire courage would not be a bad idea for the sake of being all leader-y. You can just ignore the cantrips that you get.

See this question for thoughts on making the most of the bard class.

Knight is OK for a few levels

Knight (Player’s Handbook II or here) is heavily-armored and full-BAB, and makes some solid attempts to protect others (e.g. test of mettle). Unfortunately, the knight’s code is extremely strict, even stricter than the paladin’s in a lot of ways.

It’s often said that knight has five good levels: 1, 2, 3, 4, and 20. If you go for knight, test of mettle and bulwark of defense are probably your best bets.

If you can, refluff a barbarian

Instead of rage (or ferocity or whirling frenzy, which are probably more appropriate to you), call it something else: In the Zone, Focus, something. Refluff it as bullet time or something; the mechanics still work for that (particularly ferocity or whirling frenzy, which actually do make you move faster). One level in barbarian gets you these great features, and if you have Complete Champion available, you can also swap fast movement for pounce via the lion spirit totem alternate class feature, which is a great deal.

This doesn’t directly impact leadership skills, but it gives you a lot of martial prowess to back up your leadership.

Marshals are OK if you’ve got great Charisma

If you already have very-high Charisma (16-18 before items), marshal (Player’s Handbook II) is worth it for the minor auras that add that to various things. But since you can change your minor aura whenever you like, and the major auras are weirdly weak, I don't think you need more than one level.

Legendary leaders certainly fit the bill—if your DM is using the Commander rules

Legendary leader (Heroes of Battle) gives some solid abilities on an OK chassis. The problem is that it depends on the DM using the Commander rules found in Heroes of Battle, and in my experience, most don’t. Without them, a couple of abilities don’t really make sense.

If you do go this route, note that Iron Will can be bought for 3,000 gp (Otyugh Hole, Complete Scoundrel). Many DMs won’t allow it, but it’s definitely worth asking if you can. 3,000 gp is a bit much for a +2 bonus to a single save, but as something that counts for prerequisites, it’s a steal.

Feats

Daring Outlaw would improve your damage

The Daring Outlaw feat (Complete Scoundrel) stacks your swashbuckler and rogue levels for grace and sneak attack. You need 2d6 sneak attack damage to qualify, which means three levels in rogue, or a level in rogue and a level in something else that gives sneak attack (or an analogue like the ninja’s sudden strike or the scout’s skirmish; both from Complete Adventurer).

Note that a dread commando (above) could take Daring Outlaw because sudden strike stacks with and counts as sneak attack for prerequisites. This will give you +2d6 sneak attack dice from swashbuckler levels, which is nice, and allows you to consider going back to swashbuckler for more.

Daring Warrior isn’t too good

It stacks swashbuckler and fighter, two classes you already have, which makes it seem appropriate, but they only stack for the purposes of grace and qualifying for fighter-only feats. With the exception of Weapon Supremacy (Player’s Handbook II, requires Fighter 18), the fighter-only feats are pretty weak, and grace isn’t too great.

Knowledge Devotion is pretty solid

If you have Knowledge skills, it’s an attack and damage bonus. Just worth mentioning because it’s a good feat that might fit the character. Depends whether or not your wit is backed up by real knowledge, though, since Knowledge Devotion does require a fair amount of, ya know, devotion to knowledge.

Conclusion

A bunch of dips for useful abilities

I like Barbarian 1, Bard 1, Chameleon 2, and Master of Masks 1 best of the options presented that are on your list of legal material. I wouldn’t take more levels of any of these classes, however. That gets you to 10th-level, anyway. After that, I suppose dread commando and/or legendary leader are probably your best bets.

The simple option: Daring Outlaw and dread commando

The other option is to not bother with any of that hodgepodge and just go Swashbuckler 13/Fighter 2/Dread Commando 5 with Daring Outlaw. That gets you full BAB, 7d6 Sneak Attack, and 3d6 Sudden Strike. Of course, that assumes you can get Dodge and Mobility... Anyway, it will make you a reasonably effective melee combatant and give some minor bonuses to those around you. It’s not the best build available but it does have a certain elegance.

I really do have to mention warblade again

If you can get it allowed, I have to mention again how perfect warblade is here. With a start of swashbuckler 3/fighter 2, you can do really well by taking three other classes, and then taking warblade at 9th to start with an Initiator Level of 5, thereby starting with 3rd-level maneuvers and stances. My preferences for those three levels would be Factotum 3, Chameleon 2, Barbarian 1, Master of Masks 1, and/or Bard 1 (such that they add up to three, of course). For bard, Song of the White Raven becomes your obvious choice as 9th-level feat.

This winds up getting away from the idea of the hulking thug rogue/barbarian; the solitary barbarian level is used to grant mobility and agility rather than strength and endurance. That said, this is a very vicious combat build with lots of dirty tricks, very capable of pouncing on opponents unawares and tearing into them in an unholy frenzy.

The Assassin

For a low-optimization, low-magic campaign, where you want to focus on stealth and skills but still be able to deal the hurt, you could do a lot worse than the core assassin prestige class. It gets a number of low-level spells, so it should not be a problem for low-magic, but if there’s little magic available, you definitely want what little you can get.

If alignment is an issue, consider the avenger: it replaces the Evil requirement with a Non-Chaotic requirement, which is often much more amenable to characters.

Spells

Spells are the reason you go this route. The assassin spell list is quite solid, for as small a list as it is, and it will likely fly well in a low-magic game.

This recommendation does assume that you have access, at the least, to Spell Compendium. The core assassin spell list leaves a lot to be desired. If you want to use the avenger, also make sure your DM is OK with adding the Spell Compendium assassin spells to the avenger list. That’s in line with the guidance in that book for non-core spellcasting classes on pg. 3, so it shouldn’t be a problem, but it’s a conversation you should have.

Psionics

The psionic assassin from Secrets of Sarlona also exists, and adds the very interesting option of using Expanded Knowledge for psionic minor creation, which is an excellent way to get poisons. That said, unless your DM allows other assassin spells to be converted into psionic counterparts, it’s not a great option. If you can, then you might as well?

Death Attack

Don’t focus too much on Death Attack; at best you can attempt it during a surprise round after spending three rounds studying your target out of combat. Attempting to hide and wait three rounds mid-combat is always a bad play.

Poison Use

Poison Use is meh; if you want to use poison, you want the Master of Poisons feat from Drow of the Underdark anyway. That said, Master of Poisons is a quite-solid feat, and Craft (poisonmaking) can get you poison at a huge discount (if you have a source of materials, ⅙ market price). Poisons provide a way to apply debilitating effects along with straight damage. See the Arsenic and Old Lace handbook for more details if you’re interested in going for poisons.

Again, if you are avoiding being Evil, you have to clarify something with the DM: poisons, according to Player’s Handbook and Dungeon Master’s Guide, are not evil, though usually illegal (and always dishonorable, which is why they are barred to paladins). Book of Exalted Deeds, however, says they are actually Evil – and then gives a definition/explanation of how and why they’re Evil that would include, for example, the natural poison of the couatl, that is, a notably Good creature. Book of Exalted Deeds is not a good book. Just make sure, if you don’t want to be Evil, that your DM agrees that Book of Exalted Deeds is stupid, and poisons aren’t any more inherently evil than swords.

Hide in Plain Sight

It’s a long time coming, but getting Hide in Plain Sight, along with taking the Darkstalker feat from Lords of Madness, will prevent a lot of the major ways to simply shut down your stealth. Highly recommended.

The Black Dog

This prestige class from Dragonmarked stacks with assassin levels for Death Attack DCs, and has a couple of excellent abilities aimed at poison. I’ve decided that poison is a good direction to take this, hence its appearance here.

The black dog requires the Mark of Hospitality feat, which in Eberron is limited to halflings. This is a matter of setting fluff, so if you aren’t playing in Eberron, the Mark of Hospitality might be available to half-orcs. On the other hand, I actually like halfling a great deal more than half-orc here. It does mean a shift from Strength to Dexterity which you may find undesirable, but half-orc is quite weak, and the halfling’s size is basically all to your benefit (average of −1 on damage rolls, but +1 attack, +4 to stealth, and +1 to AC). The existence of the strongheart halfling (Forgotten Realms Campaign Setting) really seals that deal.

Suggested Build

Strongheart Halfling Rogue 3/Barbarian 1/something 1/Black Dog 5/Assassin 10

At Rogue 2, the Penetrating Strike alternate class feature (Dungeonscape) is key, and at Barbarian 1, you really want the Lion Spiritual Totem alternate class feature (Complete Champion) to get Pounce instead of Fast Movement (you’re not a charger per se, but you do want to maintain mobility and full-attacks, and pounce is a really good way to do that).

I’d replace Rage with Ferocity, though I’d also consider Whirling Frenzy.

The something 1 I’m not sure about; barbarian 2 is OK but not great, rogue 4 is fairly mediocre...

Some options that should be no problem:

• Fighter. You want Weapon Finesse at this point, so that’s a use for your bonus feat, and the Hit-and-Run Tactics alternate class feature from Drow of the Underdark trades some armor and shield proficiency you probably won’t use for +2 to initiative and Dex-to-damage vs. flat-footed foes, which is awesome.

• Ranger. Simple: full BAB and 6+Int skills. Boring, but functional.

• Anything that gives Sneak Attack +1d6 at first level. Again, boring, but functional.

Some options that probably aren’t allowed, but could be awesome:

• Cleric. Best single-level dip in the game, bar none. Could be worth it even if you get none of its spells. Domain granted powers are awesome, and failing that you can trade them for Devotion feats (Complete Champion), many of which are excellent. Turn/Rebuke Undead is excellent for Divine feats, including the amazing Lolth’s Caress (Drow of the Underdark). While a halfling who worships Lolth is weird, with this build’s interest in poison it’s not a stretch to worship the goddess of spiders. Or if Lolth doesn’t exist in your setting, maybe you can just ignore that requirement.

• Ardent or Psion. One level is sufficient to manifest psionic minor creation, which will get you a plant-based poison that lasts an hour. Not a bad deal at all.

• Swordsage. Cloak of deception provides instant flat-footing for an enemy, once per encounter, while shadow jaunt provides great mobility. Wolf fang strike and sudden leap allow you to continue to dual-wield effectively even when you’re forced to move and cannot charge. If you later take Martial Stance, you can snag assassin’s stance for +2d6 Sneak Attack damage.

Anyway, you definitely want the Craven (Champions of Ruin), Darkstalker (Lords of Madness), Master of Poisons (Drow of the Underdark), and Weapon Finesse feats. Plus, black dog requires Mark of Hospitality (Eberron Campaign Setting).

The feats Extra Rage (Complete Warrior) and Wild Cohort could be very nice for you, if you can squeeze them in (maybe later, or if you take a Fighter level and have another feat to play with). Note that I don’t recommend Wild Cohort so you have a pet fighting alongside you: I recommend it so you have a reliable, cheap poison dispenser following you around. Unfortunately, both feats are kind of lackluster by the time they fit into the build I am proposing.

Anyway, your feats may look like this:

• Bonus racial feat: Weapon Finesse
• 1st-level feat: Master of Poisons
• 3rd-level feat: Mark of Hospitality
• 6th-level feat: Darkstalker
• 9th-level feat: Craven
• 12th-level feat: Extra Rage?
• 15th-level feat: Wild Cohort?

With this combination, your attacks hit hard, and you are hard to find. You have poisons that you can use selectively, and they are very dangerous. You have a smattering of spells that will make a huge difference in a low-magic world. Seems like a pretty solid approach to me.