I try to forget those in between years of of System 7 / OS8 / OS9. They all gave me deep scars through countless hours spent troubleshooting extension conflicts. All while seeing the unhelpful, literal bomb icon dozens of times in a row [0]. The windows BSOD was bad, but at least it never mocked you about the OS blowing up.
More details: In theory, extension troubleshooting should have been easy. 1) Boot with them off. If it boots, it's the extensions. 2) Turn half off. If it boots, you know it's the other half. 3) Repeat step #2 with the remaining extensions until you find the offending one.
Except it wasn't always a single one. It could be a problem that only occurred when a combination were active. So you'd go through the much higher # of combinations of turning certain groups on together... the first 5 & third 5 extensions, etc... Sometimes even that wouldn't work, and you'd be stuck opening programs you knew used certain extensions to force them into activity. Eventually, if you were lucky, you'd find the one corrupt extension and reinstall it. But if all else failed, you backed up the data with all extensions disabled, blew out the OS with a clean install and reinstall all the programs & restore the backup.