I'm not trying to be insulting, I know you have a lot of experience. Probably, like me, you expected the CK to be easier after all the experience we have now, but I'm finding it to be a royal PITA.
So, you have a couple of things going on. The initial guy's dialogue isn't working and he's not got an alias, right?. If the quest that is driving his dialogue is running then his dialogue is available to be playing so that's problem number one: Why no dialogue? If you have no sound recorded for that dialogue I suggest you do that first and see if that gets him talking. If it doesn't then go from there, but simple dialogue in the CK works like simple dialogue did in the Geck (some of the mechanics are different, but if you have stuff linked or even if you don't, if you have the GetIsID and you have at least one topic as a top level topic with appropriate conditions that are being met then you should be getting dialogue; at least I've been able to once I solved my sound issue and other people have been all over the forums with similar sound issues (and if you are doing this as part of a scene I've seen a tut that says no sound recording in your dialogue that's part of a scene can bug a scene).
The second issue you have going on is what you've diagnosed as alias stuff. If your quest is running why isn't the aliased item being added to the actor's inventory? What are you doing exactly to add that item into his inventory? How have you set it up? I probably can't help with this because I've only started working with any aliases today, but someone else will be able to help more with details.
Oh, I'm taking no insult. (Sorry if I made it seem that way

)
Does the SQV show your aliases as filled? Are they pointing to the correct references?
Okay well I'm making some progress.
I recorded quick sound files, however once ingame I noticed something. Among all the rabble of the Riften Square, if I jammed E I would see my NPC's generic hellos flicker up, so he has dialogue. However, that's run from a different quest. Also, using SQV I now notice that my alias's are all broken. They say something like:
REF 'Merc Leader' -> NONE
So they aren't being assigned? None of the three of them are. They all say -> NONE. Is it maybe that when the quest starts, first it assigns alias's then runs over dialogue, so its hanging on teh alias's for some reason, and never gets to my guys dialogue? Also, I said his dialogue worked before; it worked before I added alias's. So clearly they are the issue.
Now, onto how they're set up. I have three types. One is a reference of a dead bandit. I made a custom form, and the alias is a 'Unique Actor' directed toward the unique actor I made. That's about it for that alias. The next one is for a pedastal, an activator placed in my world. It's a 'Specific Reference' directed toward the reference I placed in my cell. The last one is a 'Create Reference to Object' where I made my own MiscItem, and said 'Create In' my previous alias, 'Merc Leader'. (The dead body)
None of these get assigned, and I think the quest hangs on it and breaks. What exactly am I doing wrong here? Can I not assign a 'Unique Actor' alias to a dead corpse? I'm trying a Specific Reference instead to see if it works. Though I have to make this an esm to test so this will take a few minutes...