I'm a new Bears fan thanks to them drafting Fields/the Texans becoming a religious ministry instead of football organization. I became a fan of this team with an open mind and wanted to just see where the team is at after watching some games and then preseason snaps with relevant players.
If the team goes 0-2 or 0-3 to start, my hopes are two-fold - 1) they start Fields the rest of the season (assuming he's healthy) and 2) they consider trading veterans for draft picks and commit to a rebuild. Committing to a rebuild means trading guys and maybe not necessarily where they want to be traded. Don't give guys de-facto no-trade clauses when they're not worthy of it. Regardless of record, Fields should start sooner rather than later.
Right now they're in an awkward stage where the best pieces on the defense are on one timeline (likely the downside of their career in terms of peak performance) while the best offensive pieces are on another timeline (the beginning of their career and not yet in their prime). It doesn't mean the season is over right away but it does mean a hard, honest assessment of the state of the team will need to be done regardless of record before the trade deadline.
If it doesn't look like the playoffs is likely closer to the trade deadline, then I would hope they'd make a pivot full on to a developmental/rebuild stage and try to trade veterans on both side of the ball for maximum value. If you don't honestly think the team is winning the super bowl this year or next year then use this year to kickstart the rebuild. Commit to Fields, trade the guys that don't have team friendly contracts and who may be close (if not already on) the downside of their career.
If you commit to the rebuild, don't do it half assed. Cut or trade the bad contracts and deal with a large dead cap penalty for 2022-2023 but have a cleaner slate for 2023-2024. I'd rather suck while Fields is learning how to be a QB in the NFL than wait until he's good but inadvertently wasting those seasons because they're still trying to clean up a bad cap situation.