Problems launching Classic, solutions
MacFixIt reader Rod Yager reports a fairly typical issue with Classic startup:
"Classic starts normally the first time after a reboot. However, if I quit the Classic environment and try to restart it, it hangs at the point where it has just displayed the Welcome to Mac OS screen. This happens even if I use the Classic control panel's advanced tab and tell it to start with extensions off - it then hangs at the point where it has displayed the Welcome to Mac OS Extensions Off screen."
Deleting Classic Support In Yager's case, the solution was to delete Classic Support and Classic Support UI from the OS 9 System Folder, and then restart the Classic Environment.
Yager writes "(After deletion) I get a dialog telling me that Classic needs to update files in 'System Folder.' Permitting it to do the update allows Classic to start normally. However, I need to do this each time I wish to restart Classic, unless it is the first time Classic has been used after an OSX restart."
Extensions Apple has some additional suggestions for resolving Classic startup issues, including isolating and eliminating extension conflicts.
Knowledge Base article #151909 states: "If the Classic environment fails to start or stops working occasionally, or some Mac OS 9 applications freeze or quit suddenly, you may have a problem with the extensions you have installed. You can use the Classic preferences pane to control the extensions you are using."
Feedback? Late-breakers@macfixit.com.
Resources

updated to 10.3.4. Never have seen any problems. Starting and restarting
classic works fine with me. Most often I use an old version of Adobe
Photoshop on classic. It has worked fine on three restarts today.
Bob Gallant