All they need to do is stay healthy. I would say they are already packed with superstars, so there's no reason they'll fail in the playoffs or have an early exit. This team, with Lillard now, is already a championship contender, probably the best in the East. They could even beat the Celtics, who I still consider one of the best.
Lillard may have a similar role with the Bucks, playing the point guard position, but it's very different here. His teammates are dominant in the paint and excel in defense compared to the Blazers, whose weakness was defense. That's one of the reasons why they sometimes exited the playoffs early, even during the time of CJ and Dame, who were one of the best backcourt duos. But now, it's not just one superstar playing with Dame; there's more than one, and I would consider Middleton a superstar too, given the massive contract he earned with the team.
Yup, Dame got more backup or better to say companion on his chase for winning a title, if competitiveness will develop among them and
a good brotherhood blends up. This squad is surely going back to the playoff, then maybe winning a title.
More on how they will adjust and sacrifice their individuality to fit on each other, I would say if Giannis and Dame will play with the same
companionship of Steph and KD way back with the Warriors, then we will see them dominate first in the east, then for the world title.
Too early though, but doable if good blend and chemistry will develop trust from each other's back.