I really like that this quest is so challenging.  Thematically, it should be a very challenging quest.  Personally, I won't care if I never save Lake-town from being destroyed, but I want a decent chance to defeat Smaug.  (I'm not as uncaring a human being as I made that sound.)

However, I have heard that it is nearly impossible to defeat Smaug, given the difficulty of the quest.

Since Smaug is immune to player card effects, I think that the way I'm going to defeat Smaug is to create a custom "Black Arrow" objective card that, under the exact right conditions, can take Smaug down.

What about something like this:

The Black Arrow - Objective

When Revealed: Attach to a hero with Ranged.  Otherwise, discard this objective and deal 1 damage to Lake-Town.

Counts as an attachment with the text: "Action: If attached hero is attacking, and his owner has no cards in hand, discard this card to make him attack +20."

Shadow:  Place 2 progress on the current quest and resolve the "When Revealed" text on this card.

I know it makes killing Smaug a lot easier, but I think I'm going to need it.  :)

Now that The Black Arrow has been previewed as a player card, I won't need to use this objective.  But I still think I'm going to need something else to make this winnable.

But I'll wait until I've played this a half-dozen times before seeing exactly what I'm going to need.