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You already answered question 1. I would answer question 2 if I thought it was relevant considering your build idea.

Shadow Fire is an absolutely horrible power, especially considering you're losing a level 17 rogue power to pick it up ... in fact the combination of all of the feats you've taken regarding Assassin's Shroud end up with a lower Nova potential than keeping the level 17 rogue power you gained through Scoundrel Training. Tumbling Strike is at level 17 and is considered one of the most powerful striker powers in the game, it combined with Low Slash (from taking Adroit Explorer as your PP), and two Melee Basic Attacks (with AP), and then feats spent on actually useful things, is going to be roughly double if not tripple the damage you'd get from all of that Shroud optimization and Shadow Fire.

Appreciate the build advice, though the 2nd question still remains unanswered. The idea of the character is to make lots of attacks in the first round, hoping for crits (edit: and I realize that minor action attacks would be helpful). For this purpose Shadow Fire has a use, though it loses some of the optimization potential if it combines poorly with Unerring Ambush (1 extra attack roll instead of 3 extra attack rolls).

Also, the Shroud mechanic and feats are there for story reasons as well, so that's going to stay there. I picked Shadow Fire for another reason; it's a Shadow power, so it'll work with Devastating Shroud to keep the shrouds on the target. The idea is to Shift with the Samurai's power, Shift 3 more if I need to via the Master Thief paragon path class feature, Shroud the target (applying two shrouds via Killer's Insight) and then attack with Shadow Flame. With at least 4 attack rolls and critting on 18-20 I should get a crit, which means the shrouds stay and deals extra crit damage because of the Ki Focus.

Activate the Death Shroud Ki Focus to add an additional shroud, then action point with a MBA. The AP puts another shroud on the target before I attack, so it'll have 4 Shrouds on it for that attack (2 shrouds for the Shadow Fire attack, 4 shrouds for the MBA, which are removed after the MBA) and rolling twice will hopefully crit again, dealing more extra damage for the Ki Focus crit effect.

I know it's a specialized build designed to do a specific thing, and there's other campaign reasons for not making it technically more powerful, but those aren't relevent. My main question is about the interaction between Unerring Ambush and Shadow Fire.

Okay, thanks.

I know this is going to be an unpopular answer, but I need to say it.

 Why do you need to say that? It's not at all relevant to the purpose of the thread, nor the question I asked (which has been moved to a new thread in the appropiate forum). If you want to say that, fine. But there's no need.

 

You can't claim story reasons for needing to use shrouds and shadow fire, because those are mechanical terms; any character that can claim taking assassin multiclass, feats, and powers for a story reason can also claim sticking with powers and feats that aren't terrible for those exact same story reasons.

I didn't claim story reasons for the Shadow Fire power. In fact, I explicitly said I didn't. "Also, the Shroud mechanic and feats are there for story reasons as well, so that's going to stay there. I picked Shadow Fire for another reason". However, I can claim story reasons for wanting to use the Shroud mechanic. It could be part of how the character became an Assassin, it could be how Assassin's are represented in the game world (maybe there's no other type of Assassin in the world). Point is, you can decide to use a certain mechanic for story reasons. I didn't say I needed to use them, I said I wanted to. I don't understand why you have a problem with that.

 It's even more baffling to me because you claim your mechanical goal is to make lots of attacks at the start of combat so you can crit and do a lot of damage, and you specifically have made choices that accomplish none of that.

False. The Samurai theme increases the chances of critial hits on the first round of combat and I've taken that option. Rolling attacks twice during the first round of combat increases the chance of a crit and I've taken that feat, as well as other bits that increase the chance of me going first, such as  Superior Initiative. Using the Action Point on the first round and taking options that place more Shrouds on the target in the first round also increases damage (Death Shroud Ki Focus, Crimson Eye Action). So you're verifiably wrong about that accusation. You may not agree with those choices, but to say I haven't dont it at all is wrong.

Wanting to make bad mechanical choices that you feel are interesting because of your character's background/story doesn't make you a better roleplayer, it makes you someone who makes bad mechanical choices.

Character Mechanics and Character Fluff are entirely separate, and nothing that is set in stone in one can have any legitimate effect on the other.

You're assuming that I don't know about the Stormwind Fallacy (what you're referring to). Fluff and Mechanics can be separate and they can also be combined. The Fluff can influence the Mechanics and vice versa. Frankly, I'm a little insulted that you felt you had to get on a soapbox and lecture me about these things. I know what I'm doing and why I'm doing it.

Furthermore, your post was not helpful in helping someone optimize. Posters should help people optimize within the limits that either they set for themselves or they are comfortable with. If someone wants to play a sub optimal choice, people should help him with that, and perhaps offer other ideas, but not rant about why they feel compelled to point out the flaws in the character and player as you have done.