in Storm Bringer, Iceman mentions Chuuya punching a guy through (several) ceilings for having asked him about his past. That guy was a wholeseller Chuuya was supposed to be making a deal with for the jewel trade he was in charge of. That incident happened July 18th, and it took the guy 3 months to heal.
Now, we know both halves of skk were 15 in, well, Fifteen, and that at this time in SB, they should both be 16. Chuuya's birthday is in April, and Dazai's, June.
Since there was a time skip of a month at the end of Fifteen, the punching incident can't have been from then, as we need at least that amount of time for Dazai's birthday to have already passed. So this was after the boys' 16th birthdays, July 18th +3 months, placing SB's events at somewhere at least mid-October, even November.
The events of SB take place over like, at most, 2 weeks, between the Flags' deaths and the final fight. Then, there's another one-month skip in the epilogue, +1.5 month, so we're now at minimum in December-January range.
The Dragon's Head Conflict is said to have happened "shortly after the King of Assassins incident". Skk should still be 16 during the conflict, so we have until the end of April to get there. The conflict lasted for 88 days, nearly 3 months, bringing us to a bare minimum of it starting at the tail end of January.
What I'm saying is there was barely 6 months, most likely even less, between SB and the end of the Dragon's Head Conflict. The PM might have mostly avoided taking part in it (canon reason why they managed to take over the underworld in its wake), but they still suffered from it all the same, especially since they had just spent and lost a lot of resources during their fight against Verlaine.
Also Chuuya must have had like 3 months to make those friends before losing them too.
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