How to optimize a rogue for highest attacks/round and damage/attack?

Question

Using only the 3.5e Player's Handbook and Dungeon Master's Guide, how can I make my rogue the most powerful possible?

What I have so far:

Professor Peppy Littleman - Halfling rogue, level 5

Str 10, Dex 22, Con 10, Int 18, Wis 12, Cha 11

24 hp, two +1 daggers, Gloves of Dexterity +2, 900gp, Chaotic Evil, Leather Armor (+2 AC)

Feats: Weapon Finesse and 2 Weapon Fighting

I was planning on taking a Fighter dip at level 8 to immediately get Improved Two Weapon fighting and another Dex point, along with Improved Initiative at level 6.

I put nearly all of my 108 skill ranks into regular rogue-type skills (bluff, hide, move silently, sleight of hand; along with spot, search, listen, etc.).

My campaign is mostly fighting humanoids and sometimes undead in city-, crypt-, and random buildings–type environments.

I have also talked to my DM about possibly using a permanent polymorph later on in the game (level 12+ or so), and he seems to be okay with it, as long as it isn't too overpowered.

I'm trying to get him to hit as many times as possible per round and as hard as possible, with and without sneak attack taken into account.

Answer 1

A few suggestions. Some of which may require your DM to be fine undoing decisions already made.

I don't know what system you used for picking stats, but I would say for a powerful rogue you have them in the wrong order.

For a general purpose rogue, I would say dex > cha > con > str > int > wis. If you want a more combat focused rogue, drop cha down behind con and str.

Int is not needed to any huge degree (in a 4+ person party), a rogue will already have enough skill points without taking such a high int. You are better off having higher cha and being better at a smaller number of skills. If the party is 2-3 people, then maybe more utility is worth the tradeoff.

The 12 wis (higher than str or con) is unlikely to provide you with too much mileage. The bonuses to spot and listen aren't going to be all that important for you (unless the DM pits you against lots of enemy rogues), and I would say the +5 hp and +1 fort save will keep you in the fight more than the +1 will save.

In a few levels time, you should be getting enough money that you can get a ring of invisibility. This is critical. It will increase your damage (sneak attack more often) and your survivability.

If I were you, I would not worry about improved initiative. Once you have the ring of invisibility, you wont be targeted before you attack people, and you don't really want to attack (and thus become visible) before the other melee characters have got in. Most rogues have the problem that they go first, and don't want to. Instead, I would go for weapon focus, or for iron will (+2 will save) if there are lots of spellcasters around.

I would recommend against taking much of a fighter dip. Unless your enemies are mostly undead. Each level you are taking in fighter is a level that doesn't give sneak attack damage and doesn't give hide/move silently as class skills.

Answer 2

Your ideas on building an optimal DPR rogue class/skill/feat wise already seem perfectly fine to me, so I'll focus on magic item optimization for DPR instead.

Unless there's a specific reason your character uses daggers, use short swords instead

The only reason I would imagine that you would use daggers instead of short swords would be if you wanted to throw those daggers on a fairly regular basis; in that case, I'd advise using just ordinary daggers and enchanting a pair of short swords instead. An average of .5 more damage dealt per attack might not be a lot (1d3 versus 1d4), but there's usually no reason not to do such a thing.

For Weapons, keep the enhancement bonus at +1 and stack effects

With weapon finesse and gloves of dexterity, your character should have little trouble hitting enemies multiple times per round even without a large enhancement bonus; you'll ultimately do more damage per round with these enchantments than with the +1's you'd otherwise get. I'd recommend stacking effects on your weapons to help you deal more damage on each hit; I'll go over a few you should or shouldn't take for various reasons.

Flaming/Frost/Shocking An extra d6 energy damage is almost never bad; although you will eventually end up encountering monsters with energy resistances at higher levels, rendering some (or all!) of these enchantments useless for the encounter. Take these early for maximum effectiveness.

Undead Bane Assuming you're going to be fighting undead periodically throughout the whole campaign, I'd recommend this as an investment. It's a +1 equivalent and it gives you 2d6 damage against those pesky sneak-attack-negating undead, as well as the equivalent of a +2 bonus against them. This is recommended instead of Holy because of your character's alignment.

Speed As long as you don't want to rely on allies giving you haste (or the limited duration on Boots of Haste), put this on only ONE weapon, since the effects don't stack. It gives you an extra attack with said weapon at your highest base attack bonus, but is an enhancement total of +3.

Keen Don't get this; get a scabbard of keen edges (or two) if crits are important to you.

Vicious If you're not worried about becoming a massive glass cannon, get this. It'll deal you a d6 of damage for every attack you hit with but deal them 2d6. Up to you to choose

Choose other magic weapon abilities at your discretion.

Other magic gear

I've already mentioned the Scabbard of Keen Edges, and you look to be going for the highest level of Gloves of Dexterity you can afford already, so I'll just cover one more slightly less than obvious edge case. A Ring of Invsibility, along with Moves Silently enchantments on your armor, can help you get into position to execute that all-too-important string of sneak attacks you want to pull off. The Ring does cost 20,000 GP however, and creatures with True Sight will see right through it, so Shadow enchantments on your armor may ultimately be more effective.

This answer is mostly intended to be supplementary to other answers, since it only covers magic items.

Answer 3

With only the DMG and PH to draw from, you've not a lot of options, but here's how you can

Hit Often & Harder

Below's a build that does what you want it to do.

Prof. Littleman, Male Halfling Bbn1/Ftr2/Rgr2/Rog13/Blackguard 2

 ----------Level----------        
 Character   Class          BAB  Feats                               Sneak Attack
    1st      Rogue 1         +0  Two-weapon Fighting (PH 102)            +1d6
    2nd      Rogue 2         +1                                          +1d6
    3rd      Rogue 3         +2  Weapon Finesse (PH 102)                 +2d6
    4th      Rogue 4         +3                                          +2d6
    5th      Rogue 5         +3                                          +3d6
    6th      Rogue 6         +4  Quick Draw (PH 98)                      +3d6
    7th      Rogue 7         +5                                          +4d6
    8th      Rogue 8         +6                                          +4d6
    9th      Rogue 9         +6  Improved Two-weapon Fighting (PH 96)    +5d6
   10th      Rogue 10        +7                                          +5d6
   11th      Rogue 11        +8                                          +6d6
   12th      Rogue 12        +9  [choice]                                +6d6
   13th      Rogue 13        +9                                          +7d6
   14th      Ranger 1       +10  Track (PH 101)                          +7d6
   15th      Ranger 2       +11  Rapid Shot (PH 99), Greater             +7d6
                                 Two-weapon Fighting (PH 95)
   16th      Barbarian 1    +12                                          +7d6
   17th      Fighter 1      +13  Power Attack (PH 98)                    +7d6
   18th      Fighter 2      +14  Cleave (PH 92), Improved Sunder (PH 96) +7d6
   19th      Blackguard 1   +15                                          +7d6
   20th      Blackguard 2   +16                                          +7d6

Prof. Littleman flanks with his allies and stabs the crap out of folks until he can afford a ring of blinking (DMG 230) (27,000 gp; 0 lbs.). After he's bought the ring--typically at character level 9, but maybe 8 if he's content throwing rocks for a level--his weapon of choice becomes flasks of either acid (PH 128), alchemist's fire (PH 128) (20 gp; 1 lb.), or both.

With flasks and the ring, Prof. Littleman stays at range. One of the effects of the spell blink [trans] (PH 206) is to deny foes their Dexterity bonuses to Armor Class versus Prof. Litteman's attacks. As he's employing splash weapons, Prof. Littleman makes ranged touch attacks versus his foes. Splash weapons can inflict precision damage in Dungeons and Dragons 3.5.¹

Thus at character level 9, while using the ring of blinking, Prof. Littleman takes the full-attack action to make 4 ranged touch attacks that each inflict 6d6 points of fire or acid damage. At character level 15, he takes the full-attack action to make 7 ranged touch attacks that each inflict 8d6 points of fire or acid damage. This is as good as Prof. Littleman's going to get until character level 20 when his number of attacks increases to 8.

The real issue the Professor has is encumbrance. His light load is 24 lbs., yet each attack he can make weighs 1 lb., and there's very little he can do about that. If 3 rounds worth of flasks are insufficient, it's time for Prof. Littleman to employ the Use Magic Device skill on that tucked away scroll of teleport [conj] (PH 293) (DMG 240) (1,125 gp; 0 lbs.) or to find cover or concealment and make Hide and Move Silently skill checks while he while quietly retrieves additional flasks from his Heward's handy haversack (DMG 259) (2,000 gp; 5 lbs.).

Note 1: The levels in blackguard (DMG 181-3) are to eek out those final +2 points of base attack bonus while A) getting class features, and B) avoiding an XP penalty for multiclassing (PH 60)--if the DM enforces that rule--after the Professor reaches epic levels.

Note 2: Taking 2 more levels of blackguard for +1d6 sneak attack is an option by replacing the level of barbarian and the second level of fighter, but doing so requires taking the feat Power Attack at character level 12 or taking the rogue special ability feat and picking the feat Power Attack.

Magic Items

Beyond the ring of blinking and items that improve the Professor's ability scores, Armor Class, and saving throws, the Professor will want a melee weapon or two. A wand of flame blade [evoc] (PH 231) (2nd-level spell at caster level 3) (90 gp/charge) creates an effect that's incompatible with the feat Weapon Finesse but nonetheless allows the Professor to make melee touch attacks for damage therefore inflicting sneak attack damage when the foe's susceptible. Later, the weapon special ability brilliant energy (DMG 224) (+4 bonus)--considered overpriced by many--permits the Professor's attacks to ignore armor bonuses and shield bonuses to Armor Class, which, while not as good as a touch attack, allows him to employ the feat Weapon Finesse.

Given the Professor's Strength, Small size, and the dearth of magic items in the DMG that grant an effect like the 4th-level Clr spell freedom of movement [abjur] (PH 233) (e.g. the ring of freedom of movement (DMG 232) (40,000 gp; 0 lbs.), for 1 hour/day if a 10 is rolled on the SRD's epic minor artifact Olidammara's dice (ELH 152) (artifact; 0 lbs.)), initially a scroll then a wand of freedom of movement is a good investment. The blackguard and ranger facilitate this purchase by having the spell freedom of movement on their spell lists.

Dealing with Creatures Immune to Precision Damage

Constructs, oozes, undead, plants, creatures with the incorporeal subtype, and elementals (COUPIEs) are the creatures types in the core rules that are immune to the rogue's sneak attack damage. There's little the core rogue can do to mitigate that immunity to precision damage. However, unlike the fighter--who lacks Use Magic Device as a class skill and probably dumped Charisma, too--the Professor should be able to employ the Use Magic Device skill to cast a spell from a scroll or wand that will solve his COUPIE problem. A scroll of limited wish [univ] (PH 248) (7th-level spell at caster level 13) (DMG 240) (3,775 gp; 0 lbs.) is a good last-ditch response to a host of ugly questions.

---

1. Splash weapons can't deal precision damage in Pathfinder.

Answer 4

To Maximize your number of attacks:
If you are not dead set on daggers you could dip into Monk for an additional attack via flurry of blows and do your two weapon fighting with unarmed attacks or Monk weapons ( for example Kamas which you could style as curved daggerlike weapons if you like the image). With you current stats that would net you:

Contra:

• -1 AC(-leather armor + wisdom to AC)
  
• -2 to-Hit on Full Attacks
  
• -1 BAB
  
• worse critical threat range (20 instead of 19 - 20)
  
• -4 Skillpoints

Pro:

• +1 Attack Per Round (on a full attack)
  
• +1/+2 to All Saves (depending on your LVL and the rest of your build)
  
• better Base Damage (1d4 instead of 1d3)
  
• improved unarmed Strike
• Monk Bonus feat

Answer 5

As a Rogue, probably the two most important tools in your arsenal are Sneak attack, and your list of skills.

Items that you're going to buy include the following:

Gloves of Dexterity- Bonuses to survivability and chance to hit are a must.

Ring of Invisibility- Helpful in getting out of trouble if you get in above your head

Blurstrike weapons- A +2 enchantment that makes your opponent flat-footed for the first attack every round. ( Will help you get sneak attack 100% of the time )

Sword of Subtlety- A +1 short sword that will give you a +4 bonus to attack and damage rolls when utilizing sneak attack. ( Effectively a +5 weapon when sneak attacking for a low price )

Scabbard of Keen edges- Keen with your weapons is pretty useful if you don't have the feats to pick up Improved Critical. ( Which you likely won't, being a rogue and all )

Ring of Blinking- 50% miss chance for melee attacks, and a chance to completely avoid the effects of any targeted spell will keep you alive much longer in melee. Denying an opponent their DEX to AC also means that you get sneak attacks on them.

Speed Weapons- A +3 enchantment for an extra attack a round is nice.

Those are probably some of the best items you can net to get yourself into a good position safety-wise. Anything that lets you sneak attack things that normally are immune to sneak attacks should be considered a must-have item.

A two level dip into fighter will net you two bonus feats if you're needing feats real bad. Anything more than that is probably a waste.

If you're a rogue with unarmed damage you can utilize Snap kick for bonus attacks.