Help Optimizing an Assassin

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I know the Assassin is considered to be generally terrible and that concept wise an Avenger would be the better option. However, the level of optimization across my group varies from low op to high op and since it's all over the board I figured this would be a good chance to play a class I thought would be interesting without hurting my party. So I would like help optimizing my build to be the best that it can be. I've discussed some of the more heavily debated aspects of the Assassin with my DM and here is what he has ruled:
1) Black Flame Form's and Shade Form's sustain minor doesn't over write the until you attack part of it's description.
2) Flurry of Talons and Shadow Fire deal 1d8/1[W], 3d8/3[W], or 6d8/6[W] depending on how many times the three attack rolls hit.

Level 30 Snapshot
====== Created Using Wizards of the Coast D&D Character Builder ======
Level: 30
Race: Human
Class: Assassin
Guild Training: Night Stalker
Form: Shade Form
Theme: Sohei
Paragon Path: Soaring Blade
Epic Destiny: Deadly Trickster

FINAL ABILITY SCORES
STR 12, CON 20, DEX 28, INT 12, WIS 15, CHA 26

STARTING ABILITY SCORES
STR 10, CON 18, DEX 20, INT 10, WIS 13, CHA 18

AC: 40 Fort: 42 Ref: 41 Will: 41
HP: 161 Surges: 11 Surge Value: 40
Initiative: +24 Speed: 6

TRAINED SKILLS
Bluff +28, Perception +24, Intimidate +28, Insight +24, Acrobatics +32, Endurance +25, Stealth +29

UNTRAINED SKILLS
Arcana +16, Athletics +16, Diplomacy +23, Dungeoneering +18, Heal +17, History +16, Nature +17, Religion +16,  Streetwise +23, Thievery +24

POWERS
Basic Attack: Melee Basic Attack
Basic Attack: Ranged Basic Attack
Flurry of Blows: Iron Soul
Sohei Theme: Sohei Flurry
Human: Heroic Effort
At-Will 1: Inescapable Blade
At-Will 2: Shadow Storm
Assassin Encounter 1: Shadow Darts
Assassin Daily 1: Targeted for Death
Assassin Utility 2: Extra Effort
Assassin Encounter 3: Army of the Night
Assassin Daily 5: Grave Spike
Assassin Utility 6: Shrouding Gloom
Assassin Encounter 7: Echoing Threat
Assassin Daily 9: Bound by Shadow
Assassin Utility 10: Spot Weakness
Assassin Encounter 13: Flurry of Talons (lose Echoing Threat)
Assassin Daily 15: Sundered Shadow (lose Bound by Shadow)
Assassin Utility 16: Reflexive Dodge
Assassin Encounter 17: Shadow Fire (lose Army of the Night)
Assassin Daily 19: Guild of Shadow (lose Grave Spike)
Assassin Utility 22: Claim the Dead
Assassin Encounter 23: Kept old powers
Assassin Daily 25: Kept old powers
Assassin Encounter 27: Kept old powers
Assassin Daily 29: Shadow Puppet (lose Sundered Shadow)

FEATS
Human: Weapon Proficiency (Fullblade)
Level 1: Lethal Shroud
Level 2: Flurry Resounding
Level 4: Assassin's Escape
Level 6: Devastating Shroud
Level 8: Superior Implement Training (Mighty Ki Focus)
Level 10: Monastic Disciple
Level 11: Toughness
Level 12: Brutal Shroud
Level 14: Killer's Insight
Level 16: Devastating Critical
Level 18: Grave Step
Level 20: Danger Sense
Level 21: Epic Resurgence
Level 22: Epic Fortitude
Level 24: Soul in Shadow
Level 26: Killer in the Crowd
Level 28: Untouchable Shade
Level 30: Perfect Recovery

ITEMS
Shadowdance Armour
Jagged Fullblade
Death Shroud Mighty Ki Focus
Adventurer's Kit



My entire plan for my build so far is to use crit as often as possible. Since Devastating Shroud allows me to keep any Shrouds I invoked when I crit, it seems like a good strategy on keeping my damage up as high as possible. So I chose to use a fullblade and a mighty ki focus as my weapon and implement to help deal extra damage when I do crit. Since our group is so spread out we use Maptool to play on and the DM had a very hard time getting shrouds to work when they were put on enemies. As such he has ruled that the shroud will now be stacked on my character instead. The same rules apply to the shrouds but doing it this way has some advantages and disadvantages. I don't have to worry about losing my shrouds if an enemy with them dies but at the same time some assassin feats no longer work as they are written.

I know that Revenant are considered the best race for Assassins, since they have wonderful feat support and great class features. however, playing as one with the lore of the world the DM has created and our current party setup would be a bad idea. I mc'd into monk just to get access to the Soaring Blade paragon path. I was originally going to mc into Avenger but decided against it for two reasons. The main one being since Oath of Enmity only applies to melee attacks that excludes half my powers. The other being it would be a nightmare to code in Maptool for only two turns worth of rerolls. If anyone can suggest a better mc I'd really appreciate it. I chose Deadly Trickster as my Epic Destiny because the level 26 utility is a very nice way to regain my two heavy hitter powers.

My ability scores are very high, my group has a -31 point buy in. Back when the group first started using the character builder the DM rolled for his scores and put what he rolled into the cb. The amount of points he had there is the amount of points listed there was the amount of points the group was allowed to use. They have been using that much ever since. We use inherent bonuses to compensate for the lack of treasure our group gets. My AC and NADs listed are without any items equipped since I do not know what level of armour I will have at the time. Also while the Assassin does not get intimidate as a class skill the DM has given it to me in place of Diplomacy. Our party is currently very diplomacy heavy and no one else has intimidate.

Thank you for taking the time to read my post and I appreciate any feedback that can be given.
The optimisation of your group is all over the place and you want to play an Assassin? I don't get this. Do you want the other low-op players not to feel alone when the high op players threaten to make them obsolete? A group's optimisation level should be roughly equal.

So your DM has ruled that you are a striker without multiattacks. That means the optimal ways to play out of an Assassin are not playing one or getting your damage from game elements that aren't class specific. Charging, Firewind Blade, etc. Crit-fishing doesn't really help you do meaningful damage until you reach epic and I'm not sure if it can be done on an Assassin.

We use inherent bonuses to compensate for the lack of treasure our group gets. My AC and NADs listed are without any items equipped since I do not know what level of armour I will have at the time.



 How is that not a contradiction?
The optimisation of your group is all over the place and you want to play an Assassin? I don't get this. Do you want the other low-op players not to feel alone when the high op players threaten to make them obsolete? A group's optimisation level should be roughly equal.


I've found the way the assassin class plays interesting for a long time. I've never actually played it since I know they have problems mechanically and that I could better serve my group by playing a different class. However, since optimization is all over the place I thought it wouldn't hurt the party to play a class that looks fun to play.

So your DM has ruled that you are a striker without multiattacks. That means the optimal ways to play out of an Assassin are not playing one or getting your damage from game elements that aren't class specific. Charging, Firewind Blade, etc. Crit-fishing doesn't really help you do meaningful damage until you reach epic and I'm not sure if it can be done on an Assassin.


I wasn't entirely sure if crit-fishing was the way to go, it seemed like a good idea though. I'll definitely start looking into some of those methods, so thank you.

We use inherent bonuses to compensate for the lack of treasure our group gets. My AC and NADs listed are without any items equipped since I do not know what level of armour I will have at the time.



How is that not a contradiction?


I admit I probably shouldn't have written this at 2:00am right before I went to bed. That sentence is a complete contradiction and makes no sense. Sorry about that.

Ok, hung around a while, but I am a new poster, so be aware of that. 
 
You might want to change your assassin's shroud power for attack finess (MY understanding according to the Assassin handbook is that you can swap out the shrouds for attack finesse, which gives you a scaling 1d8 per tier and free melee weapon training.) The human PP adroit explorer is good IF you want to critfish, since you can choose shadow darts at level 11, and then Flurry of tallions at level 21. Since the Adroit explorer gives you two uses of these tripple hitters, you can work up a decent nova.

You could multiclass into rouge for sneak attack and the better rouge powers (Low Strike) but you would be limited to using a rapier. That said, there are some charge package feats you would qualify for, cheif among them is surprising charge (Extra damage on a charge). Used in conjunction with a rapier and as many charge feats and items (Vanguard Weapon among them, not sure if you can get a Vangard Rapier though) you could charge for decent amounts of damage. 

Warlock is also a good multiclass for the Long Night Scion paragon path, which you can use to ping cold vunerability (With the Permafrost feat package and a Frostwind Blade/Frost Weapon) and auto slow. World Serpent's Grasp gives you free proning with the lv 16 feature, and if every heavy blade/axe user takes headsmans chop, your party could dish out a significant amount of damage. This works because of shadow step, your free at-will teleport. 

If you can take the Dragonmark of Shadow, then take the Thuranni Shadowkiller for a good level 16 feature (Be aware that it is Necrotic damage)

Epic Destinies are limited for a shadow class, but the Destined Scion is mechanically sound and it is easy for the DM. Keeper of the Everflow also has an amazing level 21 feature right off the bat, and there is something about an assassin who redeems souls, not just kills stuff. The Planeshaper gets a mention despite boosting a dump stat (Int) because of its lv21 feature that let you a power twice per encounter (Pick up minor action attacks and you will love this feature,) a pesudo stun on crits that does require a modicum of thinking to use, and at level 30, auto 15 cold or fire damage (Ping Permafrost for maximum effect.) Radiant One requires you to boost a dumpstat, but boy, is it powerful if your party can get at-will radiant vunerability or fire vunerability. Be aware that the damage applies to every instance you deal damage, so with long night scion, permafrost and a frostwind blade, you coud deal very good damage with the cold annd radiant/fire damage. Only really worth it IF you can, as said, get the radiant vunerability. Demigod get mentioned as the standard to wich all other Epic Destinies are compared to, and it is as good as ever. 

If you multiclass, then you should go for Eternal Defender if you multiclass fighter Who can also do the charge op stuff, but you need at least a modicum of str (13). The Destiny gives you oversized weapons, but it is a bit anti thematic. The Primal classes get access to reincarnate champion, which you can use to get revernant and gnoll feats (Gnolls can, for two feats, use an encounter power on a charge ONCE per encounter. You are using a racial encounter power to get this.) 

Really, Assassins are dripping with flavour, but they are hard to mechanically implment.
Shadow Darts is not a triple-hit. It has "or" wording, not "and".
Assassins have some really cool item support. Check out Xenda-Dran's Array and Bracers of Assassination. I also do recommend finding a way to MC avenger, if you're critfishing there's really no better thing you can do.

Perfect Slayer ED is very nice for a pure-class assassin. I'll second Adroit Explorer as something to look at.
Shadow Darts is not a triple-hit. It has "or" wording, not "and".

I was mentioning that one has to make three rolls, each with a chance of getting a critical. You are ringht about the incorrect use of termanaology, and thanks of pointing it out.