How do you think Roose is going to go out in Winds, will he be killed by Ramsay like in the show (in a very different style, obviously) or is it something a bit unexpected?
Not fond of it being similar to the show version because it implies he's not gonna get a lot of screentime in tWoW; it's also kind of a cheap way to give him "karma" for killing robb by just reversing the roles and having roose be at the receiving end of a murderous betrayal. Note also that Theon is absent from this storyline now (since he escaped), and i'd assume Roose as an important tertiary character would have at least one more big chapter in tWoW, so he probably escapes the Winterfell situation alive at the very least until another PoV crosses his path (Asha?).
If Stannis takes Winterfell, i'd assume Roose would be a prisoner for the moment, maybe saved for a Stark to judge over as a show of goodwill; and whatever "northern conspiracy" payoff there is would probably mean that the northmen distance themselves from him as much as possible and make him the fall guy for the entire red wedding + fallout events (which are mostly his fault anyways). Barbrey as a character likely has been added to the story in aDwD to give a bit of diversity to the northern politics, as someone who is not a stark loyalist and has some closer feelings towards roose but also isnt guilty of the red wedding. I think her role might be that she is a bit of a thorn in the otherwise likely clean consensus on what to do with the Bolton problem and she might argue somewhat in Roose' favour politically (maybe arguing against him being executed or otherwise buying him some time).
And the best sword is the one that cuts both ways, he might tell you. Take the Battle of Green Fork. Had his night march taken Lord Tywin unawares and won the battle, he would have smashed the Lannisters and become the hero of the hour. While if it failed... well, you see what happened. The only way he could lose there would be if were captured or slain himself, and he did his best to minimize the chances of that. - GRRM, SSM Feb 3 2001
Roose' storyline so far has been about how he tries to maximize his profits, while also keeping out of harms way and not getting caught. He acts in ways that are morally reprehensive as long as the result is favourable to him and he can get away with it scot free. Yet come aDwD, we start to see that it is getting harder and harder for him to keep this up:
Roose Bolton said nothing at all. But Theon Greyjoy saw a look in his pale eyes that he had never seen before—an uneasiness, even a hint of fear. - a Ghost in Winterfell, aDwD
Ned Stark tried his best to act like a decent person and showed a spine acting openly as such, and after a lifetime of integrity his legacy lives on in his children and people are willing to go to war in his memory. Roose is his foil; he acts morally badly, and spinelessly so as he tries to avoid consequences - so likely as an inversion to Ned his house will go to ruin and the consequences of his actions catch up to him as his modus operandi made him liked by few. So i'd personally find it interesting if he has a fair trial and gets judged the way he deserves, with no way for him to weasel himself out of it again.
My dream tWoW direction would be that he then gets sent to the wall (which also was Ned's initial sentence, another foil moment) and becomes the epilogue PoV and faces an Other - it would be a cool way to hand off the torch from the last big human villain of the wot5k storyline to the center antagonistic force of the war for the dawn storyline (it would also complete the set of Red Wedding architects being epilogue PoVs as the first epilogue in aSoS was a Frey, and the second in aDwD a Lannister). It would also really showcase how inhuman and alien the Others are by taking the coldest and "least humane" human character that everyone jokes is a vampire, and showing that in contrast to them he still is one of us by giving us a view inside his brain and his very human reaction to them.
The real enemy is the cold. - Prologue, aGoT
Reek wondered if Roose Bolton ever cried. If so, do the tears feel cold upon his cheeks? - Reek III, aDwD
He looked deep into the heart of winter, and then he cried out, afraid, and the heat of his tears burned on his cheeks. - Bran III, aGoT