Hi, Brian -
Yes, it seems to be a "may happen" issue with OS 9.
None of the stand-alone OS 9 installers will check as to whether a machine is subject to the 8GB restriction, nor if the target volume is within that - hence it will install regardless of the potential for booting problems.
There have been some folk who had a successful initial install of OS 9 on an unpartitioned large drive on such a machine, but when they updated the OS to a later version of OS 9, they got the no-boot problem - perhaps an essential part of the OS ended up outside the 8GB space.
Since the only solution when the problem does occur is to reformat and partition the drive, thus erasing it, it probably makes sense to do that initially.
The issue with OSX is a bit different - the installer for OSX will detect when it is installing on a machine subject to the 8GB restriction, and whether a volume is contained within the first 8GB; if it is not, the installer will not permit the installation to occur on that volume.