The one issue with Orsik starting things means it is Orsik that has to make the Sleight of Hand vs perception check to gain surprise...I suppose if he's in back he could get adv.
Actually, Orsik does not need to initiate the Surprise, if we as a party surprise everyone, because he is expecting action, he can still benefit from the surprise round, couldn't he?
If they tie the ropes well enough he has adv anyway right? (I think it was if they get over 15 we get adv to untie discreetly?) And they get adv on tying since they're helping each other tie?
Regardless, I still think it's worth risking. The diff between one character getting advantage on a single shot and all of us having advantage for 10 rounds (concentration allowing) is so huge.
And not really from a rules POV...in the fiction what would be the best way to kick off the ambush and get the most out of it? Is it havr Orsik in the back untie his knots and sling a spell? Seems to me that would be a reasonable plan. Are the rules (and the rulings) supporting that? I hope so.
I think it makes sense both rules- and fiction-wise. Having one character act to try and get us all advantage (both literally and metaphorically) on our following attacks seems like a natural starting place. With any luck he might even catch more than Blopp; hopefully a guard or two will be within the AoE.
The surprise mechanic is an interesting house rule. I'd forgotten all about the disadvantage on dex saves bit until I went back and re-read the rule today (and went "oh OH OH Faerie Fire!!"). I'm garbage at remembering house rules...I think I'll go bookmark that post right now. :\
Hahah, I am fully on-board. Is there a way that 'Van and Ez can give Orsik an advantage with the casting? Ez and Van could help with his bonds so that they can easily be undone, or maybe we could actually provide a necessary distraction that may give him a little bit of cover while casting...