I'm usually one to preach patience, but I just feel like big picture decisions are going to need to be made soon. You've got two top five outfielders in baseball, one with years of team control and one who the entire fanbase wants to give all the money to, and then two behind them that are also very good and signed comfortably through next year. You can't just let Caissie and Alcantara (and probably Ballesteros) sit in Iowa until 2027. If you think that the current offense in Chicago can threaten for a championship in the next few years, you've got a lot of talent in Iowa without spots (and you've got this theoretical money under the cap this year 'earmarked' for in season additions). Sitting at 29-20 with the toughest schedule YTD (still) should lead you to that conclusion. Kicking ass for the next few weeks should help even more.
If you don't think this is the group for you (or all the doomsayers were right and payroll is being permanently slashed), then you realistically ride out this year (even worst case scenario I can't see them being sellers, barring a collapse) and hope you get lucky with a flawed roster, let Tucker walk, put Happ, Suzuki, and Hoerner on the market and start next year with a line up of like PCA/Moises/Busch/Shaw/Caissie/Alcantara/Long/Swanson/Amaya and whatever pitching you can buy. This is not what I would pick, to be clear, that's a 76 win, 'up and coming' punt of a team.
So, in conclusion, force the front office's hand. Go be 50-35 or something at the end of June. It's right there for them.