I managed the vertical orientation with the help of an extension called MacPortrait. After much trial and error, it runs flawlessly.
In the beginning, I was experiencing several extension conflicts. Even with just OS 9's "base" extensions on. The two major ones being the CD Drive and Ethernet extensions.
I basically stripped the machines extensions to the BARE minimum it needs to do the job I want it to. Not really practical if your doing anything more than playing vertical games, but I'm not... so it's perfect! Lean and mean!!!