System maintenance and start up

Hello: Thanks in advance. My system works fine 90 percent of the time. I use DVD Studio Pro, FCP, Compressor, lots of DV media, 2 External Firewire drives, etc. Maxed out on Ram and Drive Space. Nothing too crazy.
If I ever have to restart my system, sometimes it takes 20 times for me to restart before it's good to go. Sometimes on the first restart it works fine. Other times it takes 10 times and I have to manually shut down and start up each time.
How can I fix this? What haven't I done? I have used Disk Utility, Mac Janitor, etc. to try and fix. Like I said. the system works fine 90 percent of the time. Thanks.
Craig

I think you may have some serious disk repair to handle. First, try the following:
Boot from your Tiger DVD. After the installer loads select your language and click on the Continue button, then select Disk Utility from the Utilities menu. After DU loads select your OS X volume from the list on the left, click on the First Aid tab, then click on the Repair Disk button. If DU reports any errors that have been fixed, then re-run Repair Disk until no errors are reported. If no errors are reported click on the Repair Permissions button. Wait until the operation completes, then quit DU and return to the installer. Now shutdown the computer for a couple of minutes and then restart normally.
If DU reports errors it cannot fix, then you will need Disk Warrior (3.0.3 for Tiger) and/or TechTool Pro (4.1.2 for Tiger) to repair the drive. If you don't have either of them or if neither of them can fix the drive, then you will need to reformat the drive and reinstall OS X.
I would then download TinkerTool System and use it to clear out all user/system caches, font caches, etc. Navigate to the /System/Library/ folder and delete the Extensions.kextcache and Extensions.mkext files.
Then do a restart to allow the OS to rebuild the caches. If problems persist with applications crashing, then try creating a new user account and logging into that account. If the crashes cease, then there may be some corrupted preference files associated with the apps that are crashing.

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