Generally, I'd lean towards the sustainability versus all-in approach. However, at some point, I think you have to try for the latter on occasion. The Packers, to me, have had as their goal, winning the NFC North, not winning the SB. With Rodgers in his prime, adopting the all-in approach, which I don't think they have ever done, might have led to more SB appearances.
The Brewers are currently in a Rodgers-like scenario with an elite pitching staff. I think the time to go all-in, or at least somewhat, was last year's trade deadline or the offseason. They either didn't want to do it or couldn't because MA wouldn't let them. I'm not sure this team was one that could have been significantly improved to make a difference.
If the three moves they did make were the only ones they were going to make, I think I would have preferred them to do nothing. I personally would have looked to trade Hader the past two years. But with his value declining as he gets closer and closer to free agency, again not sure now was the time.