Help with Garak-type Rogue for high-level into Epic

[phaenix]

Hi all! Nice to see these spiffy new boards!

So I recently started playing in a high-level game (we started at 20th), and we have one somewhat weak link in our party, so I'd like to offer the player some help.

The party:
Me: Transmuter 5/War Weaver 5/Incantatrix 10
Summoning-focused druid (dunno if he has PrC'd. I don't think so). Traded his AC for a Spirit Companion.
Conjuror/Druid/Arcane Heirophant with a tripping-focused Familiar Companion
"Clifford the Big Red Dog" - Hound Archon/Paladin. Despite that build stub, he was hitting pretty reliably the first game. Should be easy for me to buff into effectiveness. Has a Bronze Dragon mount.
VoP Saint Cleric of Tyr - planning on using Extraordinary Spell Aimed AMFs, buffing up and beating face.

...and the guy I want to help. I'm pretty sure he's a Rogue 20, which is somewhat alarming. He had trouble hitting prone dragons (though they had pretty beefy deflection bonuses to AC). The player hasn't played D&D in a while, so I can't really blame him for accidentally bringing a knife to a rocket-tag fight.

His character is based on Garak from Star Trek: Deep Space Nine. Sort of a intrigue/diplomacy type, if anyone hasn't seen it. I'm pretty sure he has maxed Profession(Tailor) to boot. His race is Halfling, and the character is from Telflam (FR campaign).

So I immediately thought "Telflammar Shadowlord!" I'm pretty sure the DM will let us change the alignment requirements (everyone in the party is Good-aligned). I'm pretty sure we can get him the Shadow-walker template sans LA, too, if we pay the GP price.

I can drop a Dimension Jumper into my spell-storing ring, then persist it for him when he casts it on himself, so he should be able to *bamf* as a move action every turn, though he should probably have some additional options too.

So, something like

Strongheart Halfling Swordsage 1/Rogue 3/Cobra Strike Monk 2/Swordsage 1/Telflammar Shadowlord 4/More Rogue?

Trade the Monk's Evasion for Feign Death (Exemplars of Evil) - good defensive ability, sets up a full attack from a wand of Stand

Feats:
1: Shadow Blade
Halfling: Darkstalker
3: Blind-Fight
Monk 1: Dodge
Monk 2: Mobility
6: Spring Attack
9: Craven
12: Staggering Strike
15: Gloom Razor
18:

I'm a little hesitant to suggest a build that uses psionics, incarnum, or moar magic, given the player's lack of recent experience. A few ToB maneuvers should be OK, I think. If it's absoluteky, awesome go ahead and suggest it anyway, though.

Multiple Full Attacks per round is pretty sweet, but only if he can hit and do damage - any suggestions for making sure he can connect regularly and slice a few jugulars? Any feats he NEEEDS? Equipment, skills, skill tricks? Can we get him playing in the same game as all the casters? I haven't really built any rogues before, and I need your help!

Also, please suggest anything we can do to keep him viable into Epic! I'm leaning on the DM to take Epic Spellcasting off the table (otherwise it's gonna get ugly FAST, but he's talked about challenging gods and whatnot, so we may need that one up our sleeve.) Is Perfect Wight the best he can do?

Thanks!

[Vicerious]

Between dimension jumper and swordsage 'port maneuvers, I don't see him getting much mileage out of Spring Attack. I'd strongly recommend dropping Dodge, Mobility, and Spring Attack from the build entirely, unless they're prereqs for something (I'm AFB at the moment).

Picking up Weapon Finesse and cranking his Dex is a good idea since you've already got Shadow Blade. And given that SB requires you be in a Shadow Hand stance anyway, he'll get good use out of the Discipline weapon enhancement from ToB - it's a +1 that can grant +3 or more to attack rolls.

If he still has trouble hitting, see what you can do about setting him up with wraithstrike and/or one or two spectral daggers.

[phaenix]

Unfortunately, those crappy feats are pre-reqs. For Telflammar Shadowlord. hence the monk levels to pick them up. Discipline Weapon is a good call, though. And I'll lean on the cleric to drop a Divine Agility into the ring for him, too. Wraithstrike would be handy.Maybe I can get the Arcane Heirophant to spend a slot on that, since he has two sets of spells

EDIT: finished that last sentence so it made a modicum of sense.

[Vicerious]

Consider having the player spend some gold on some pearls of power if the casters are hesitant about spending slots.

Now that I'm back at my books, you should check out page 59 of the MIC for the spectral dagger.  It's 6k for what's essentially at-will chill touch.  It's not a weapon attack, so you'd have to ask your DM if he could add Shadow Blade and company to attacks with it.  If not, it's a good backup weapon.

[phaenix]

That seems like a pretty sweet mid-level weapon, but the save is only DC 11 - I'm not sure a 5% chance to do 1 strength damage is really going to cut it into epic. Also, It can't be enchanted, so my Chained Greater Magic Weapon would pass him by. Still, it's cheap enough that he could keep it in his boot just in case.

[weenog]

That seems like a pretty sweet mid-level weapon, but the save is only DC 11 - I'm not sure a 5% chance to do 1 strength damage is really going to cut it into epic. Also, It can't be enchanted, so my Chained Greater Magic Weapon would pass him by. Still, it's cheap enough that he could keep it in his boot just in case.

Pretty sure the Str damage isn't the point, there.  If you can't hit the broad side of a fat guy, and the majority of your damage is sneak attack (or anything else that doesn't care what your base damage is), a delivery system for that bonus damage that uses touch attacks is a good thing, regardless of how low its own damage is.

BTW, flasks of acid and of alchemist's fire can do the same thing for you with ranged attacks, so suggest spoonhead pick some up.

[phaenix]

You're right that sneak attack is where is damage is going to come from. I think it'll be easier to handle his to-hit problems with a persistent Wraithstrike, which will allow him to benefit from GMW and put whatever enchantments he wants on his weapons.

Good call on the flask-throwing angle. That's something I overlooked.

[Vicerious]

It might be moot at this point, but being invisible also grants a +2 to hit, besides the obvious benefits.

[solara]

And, of course, for the rp angle, he MUST have full ranks in bluff. Diplomacy is optional. If you can use Complete Scoundrel and skill tricks, might I recommend: Group Fake-Out, Second Impression, Social Recovery, and Timely Misdirection, as they seem fun/thematic/useful? And using the line, "It's all true. Especially the lies."

Props to your friend for an awesome character concept - I'm playing something fairly similar, with a character that follows a homebrewed-god equivalent of "Pelor, the Burning Hate."

[phaenix]

Those are great suggestions. I haven't seen his skills, but I'd imagine he's at least maxed out Bluff. CS is allowed (pretty much any 3.5 stuff is allowed, though I'm not sure about non-FR settings). I don't know if he's looked at skill tricks. I'll definitely bring those to his attention.

Thanks!

[Optimator]

The build you suggested looks pretty good.  One thing I've found is that melee characters in epic are defined by their items more so than ever.  A pair of Discipline (Shadow Hand) Wounding short swords would be pretty sick.

[phaenix]

Equipment is definitely going to be a big deal in Epic. I don't think we have any crafters, but he should be able to pick up pretty much anything he'll need.

The arc of the campaign is supposed to take us planar after a few sessions, so what do folks think about the Hellbreaker PrC (FCII p. 86)? There are feat-tax prerequisites, but it has some pretty handy abilities. Anyone used it before? If the player does like it, does anyone have any suggestions for an Epic progression for it (or does one already exist?)