Difficult to say. For me, it depends on the overall situation, not on a specific date. Example:
In my rebuild dynasty, my team is 3-5. I’m the underdog this week, so I’ll probably be 3-6 after week 9. Sounds like I can write that season off.
But: in weeks 10-14, I will play the 5 weakest teams in the league. Teams that I outperformed in every of the last 3 weeks.
Plus, my team is performing better and better. I just defeated both of last years finalists in consecutive weeks, and for both of them, it was only the 2nd L this season. And neither injuries nor BYE weeks were a major factor.
So there is every chance I will finish the regular season 8-6 and make the playoffs. Even a 7-7 could work, as the league is very balanced.
I will have to make my decision latest by week 11. Because our trade deadline is on Nov 29. If I want to sell some assets to load up on next year’s draft pick, I will have to push for these trades in the next 2 weeks.
Chances are I will be on the playoff bubble by then. Tricky decision.
My other dynasty is easier. I’m 6-2, #1 seed, #1 in the team power rankings, #2 in points scored - of course, I will push to defend my title.
Still a few tricky decisions to make there. Last year, I sold off some depth pieces for 2022 picks, one of which turned out to be the 1.01. I already have two extra 2nds for 2023, one early, one late. Would love to get an extra 1st, and then try to bundle picks and move up in the 1st round.
OTOH, if I want to make a push for the title, I may want to invest in some short-term depth pieces, like D’Onta Foreman. The loss of Breece Hall didn’t kill my team - I still have Austin Ekeler and Rhamondre Stevenson. But if one of them gets injured, I will have to start Michael Carter, Damien Harris or Brian Robinson - not ideal.
Still, I think I’d rather settle for 2nd, 3rd or 4th place this year, than giving up on 2023 draft capital.