Interestingly it boots with extensions off but when they are on it freezes either before the finder loads or right after the icons show up. I tried flipping them around and the daughtercard is seated well, it boots with one or the other but with both it freezes. Ideas?

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I think you have an extension conflict. You might want to download Conflict Catcher Demo and see if any extensions have conflicts. The other thing is have you had it connected to any servers that is a permanent connection? Try cleaning out your server folder and see if that helps. Try that and report back. If all else doesn't work, it may be time for a re-install of OS 9 as you may have a corrupt system