Any problems with cunning sneak / shadow walk combo?

I take Gloaming Cut under the "specific beats general" clause. The fact that it explicitly includes a stealth check to become Hidden allows it to function by my ruling.
 
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I should read the text of Gloaming Cut -- it might be a good fit for my (Rogue|Warlock)/Assassin, a tiefling named Gloom who I built to play sort of like Nightcrawler.

I've got cunning sneak + shadow walk, and I've been picking up teleport powers. I've got Shadow Step as an encounter teleport from my Assassin multiclass, Otherwind Stride as my Warlock attack 3 power, and Torog's Lamentation of the Shackled. My Rogue attack 1 power is Shadow Strike, which lets me hide again after attacking once per encounter.

On the feat front I have cunning sneak via Hybrid Talent, then the Assassin multiclass, then Cursed Shadow to pick up shadow walk. I also have Mark of Passage to boost my shifts and teleports by 1 square.

The DM has a custom enhancement system that replaces magic items and expertise feats. Its advantage is that you can mix and match properties and powers in a single item/boon slot. So I have:

  • Quicksilver Blade's power to gain a move action on a crit
  • Pact Blade's property (one implement to rule them all)
  • Sehanine's Mask of the Dark Moon property (half damage on hit and no damage on miss from enemies that can't see you)
  • Torog's Lamentation of the Shackled power (teleport away as a reaction when immobilized or restrained).
 

Charging ends your turn.

Not if you take the Daring Acrobat PP. I admit this will work only later in your career but it's one of the best ways to use the combo effectively.

A good Epic Destiny would be Raven Knight for insubstantial and phasing UEoNT whenever you charge. And if fits thematically a sort of Nightcrawler.

Going Revenant with Shadar-Kai past you can take Past Soul for another teleport, opening you the feat Dread of Sakkors that combined with World Serpent's Grasp will let you do a lot of push/prone charges. Mmmm, I'm starting to see a build here.....
 
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