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farinal wrote:
I fear they won't come out alive. What if the players turn tail and run back to the Lonely Mountain when they see the dragon? How big a damage can Raenar cause under Gibbet King's influence and unleashed on North?

With only two players, I hope you're scaling things for them to make it manageable.
But that being said, failing the mission and allowing the Gibbet King to control Raenar could make for a very interesting campaign if you're willing to put in the work.

Well it turned out well. Gibbet King has been defeated and sent to oblivion by Raenar's posion breath and now the frost drake occupies the watchtower as his new lair. At least my heroes didn't die

Now onwards to DoM!

Do you intend to have Raenar cause any ongoing problems for Wilderland?

He will stay put for some years. He will first get comfy in his lair, check his new treasure hoard and think that going south could cause trouble since there is a Dragonslayer in Dale and even the mighty Smaug got killed...but, I am most certainly thinking on introducing him once more in my DoM campaign. Perhaps the Messenger of Mordor will reach out to him or perhaps a band of dwarves will try to slay him since they know the dragon sleeps there and they are eager to prove themselves and this will go badly. I haven't really decided on how to add him again to the story but having a sleeping dragon nearby does make things interesting.

Yeah, Raenar has taken over the tower in my game as well.
I am definitely going to bring him into my DoM campaign at some point, I just haven't figured out exactly when or how. I'm currently leaning towards having him get involved when the Forest Dragon awakens.

You could also substitute Raenar for the Forest Dragon - he wakes up and slithers south, either drawn by the Shadow or just because he's in the mood for some venison.