I think the time for most of those sorts of questions was 12 months ago, and they either weren't asked or weren't answered. That's when the 2010s era of the Bruins ended, and ended in one last spectacular failure/falling short/choose your term depending on how harsh you want to be.
Sweeney and Neely had a group through 2016-23 that should have won a Cup, and didn't. But for whatever exact reasons ownership were pleased enough regardless to keep them both employed. Which means they've been handed the keys to at least start the next era. What happened in this post-window transition year, where the debts of the past were paid off, didn't really mean anything in the grand scheme of things. Celebrate the Centennial, make some money, have a low-key crack at some success, and that's it. No real expectations and no high level jobs, except possibly Monty's, on the line.
It's now we move fully into building the next gen roster and hopefully the next Cup run. The past is past and there it must stay. For better or worse, the current mob are still in charge. So the pertinent questions for us fans going forwards are how long a leash do Cam and Don have with this new era? How soon is success expected, and how much? How does the team hope to become a genuine top contender despite having an extremely shallow prospect pool? And so on. Interesting times ahead.