In general the system is unstable when booting as the result of a restart of the emulated Mac rather than a fresh launch of B2/SS.
Perhaps this is:
Emulator state not being reset in a realistic way for whatever system-level stuff (traps, toolbox calls?) the OS is doing to set up for the reboot
Some hooks into the ROM or OS established at boot time are not establishing correctly in the second session?
While it's possible to work around the lack of working restarts somewhat by just always shutting down instead of restarting when given the choice, many software installers are written to only let you do a restart afterwards, so restarts are not entirely avoidable.
In general the system is unstable when booting as the result of a restart of the emulated Mac rather than a fresh launch of B2/SS.
Perhaps this is:
While it's possible to work around the lack of working restarts somewhat by just always shutting down instead of restarting when given the choice, many software installers are written to only let you do a restart afterwards, so restarts are not entirely avoidable.