IDK Debian so have been keeping quiet but no solution has been identified yet so here goes ...
Does Debian support an /etc/fastboot file? If so, it could be time-dependently created or deleted by a boot script running before the fsck activity in the boot order.
Alternatively the boot script that initiates fsck (/etc/init.d/mountall.sh?) could be modified, making that functionality time-dependent.
It is, of course, scary to mess with boot scripts on a remote server ...
... so if you choose to try this approach you might like to simply comment out the fsck code and call another script for the new/clever time-dependent commands so if it doesn't work at least the main script continues.