I think three of the biggest issues are:
The money spent is not fully translating to results on the field.
The roster stars continue to age.
The farm system prospects are still few and the poisitional options are not coming until 2026 at the earliest.
The Dodgers are the biggest spenders in the game, but they just won the WS. Phillies are next and, outside of reaching the WS in 2022, have not seen that spending advantage pay off.
The Mets or Yanks may overtake the Phillies in 2025 spending, especially if one signs Soto, but to this point they have spent less for similar results.
I think the Casty and Turner contracts were overpays. Casty was also duplicative of Schwarber. Harper had to be since he was the cornerstone to get any of these other players to come here. JT, Wheeler and Nola are fair deals that we had no choice on. Losing them was not an option..
That gets to the other point; the younger players - Bohm, Marsh, Stott, Rojas - have shown inconsistent development that delays the timing of giving them more responsibility and moving away from the expensive vet FA focus..The reality Bohm and maybe others in this group are being dangled as trade bait highlights the corner DD has painted himself into with this roster.
The other aspect of that corner is the continued lack of prospects being developed by the farm system. Painter hopefully will come this season, but Crawford and Miller not likely until 2026 if they are not traded themselves to keep the train running in 2025.
At some point, we need to plan and invest for the future. Turner, Harper, Schwarber, Realmuto, Casty, Nola and Wheeler are all over 31 or older. We'll see how DD handles this, but the organization in a tough spot and I'm not sure I see a clear plan from him for addressing it.