I already completed the Waking Nightmare quest, I helped the sailor dude with his Void Salts problem, the old lady from the potion shop wanting the ring, and mined ore from the 2 mines and sold them to their respective owners, and still, the Jarl Skald WON'T show the another dialogue, just:

"How is Dawnstar faring the war?" and

"Is Dawnstar prepared for dragon attacks?"

I ask the 2 questions, but no other dialogue is available afterwards.

So, is there a work around this?, or one of the things I payed for when I bought Heartfire won't be available for me (Dawnstar house), because that's the house I want, and also the achivement (I'm on the 360 so no console comands).

I would like to know this as well. I did the Waking Nightmare quest before talking to the Jarl, which I'm afraid might be a mistake!

I have done it both ways and it never made the slightest difference to becoming Thane, he was happy just to be able sleep without nightmares, whether you talked to him before or after you did the other quests. And there is no work around, the next quest he gives you is the kill the giant one, and it is level locked, so you better wander off and work your way up to level 22 (or it could have been 23). If you did both quests, then speaking to the Jarl's steward might be an idea, see what might be on offer.

I am sure there would not be that many low level players in a rush to go take on a gaint anyway, they try not to give out suicide quests.