Philosophically where I align, and have been this way for years, is that the Cubs should ALWAYS have a paid true Ace and a paid #2, spending $60-70M on both arms. Every other starter should be a team and cost controlled arm.
3-5 years ago, the Cubs were not in a position to do this due to poor organizational planning, hence the Taillon, Shota, Stroman, Rae, Boyd, Davies, Williams, Smyly deals. They were $8-17M deals for #3, 4, and 5 starters because you needed arms as you had none developed.
As books clear, I do foresee the Cubs wanting to be more aligned with my philosophy - Cabrera, Horton, Steele, Birdsell, Wicks, Wiggins being cheap allows for you to get the Skubals and Peraltas. Unfortunately, 4 of those 5 now have serious injuries