Personally, I would have preferred Assad over any of the other choices for game 1 and I was shocked he was left off the roster. In spite of his low K rate, I really think one of the reasons Assad is so effective is that he really throws the entire kitchen sink at hitters so they have no idea what pitch is coming in what count and don't have the option to sit on any particular pitch or any particular location. So, facing a team that doesn't chase much and doesn't whiff much, why not lean into that? We know they don't hit many homers and their quality of contact isn't elite, so take advantage of the Cubs elite defense and the fact that the Brewers are going to swing at strikes, many of which are likely to be pitcher's pitches and likely to induce less than solid contact.
I absolutely hated starting Boyd against Milwaukee (they beat him up earlier this year) on short rest (he's so far beyond the IP he's thrown in years) when there were a lot of other options, albeit none of them ideal.