My Apple software is a nightmare lately

I've always been really happy with my Macs and the software's been a dream to use.
Until Leopard that is.
I always keep my software up to date, as soon as software update wants to download and install I always stand back and let it do it's thing.
My problems started with Mail. Then the address book. Now it extends to iTunes and my iPods.
Mail : This thing refuses to quit. 9 out of 10 times that I ask mail to quit, I end up having to force quit it. So many times has it stopped shut down of the Mac.. I am getting tired of this.
Today I sent an extremely urgent mail to a client, two hours later he called me and asked "Uh.. where's my email man?" Turns out mail had frozen. After a force quit and a relaunch, the mail was sent. No error message, nothing.. It just froze without me knowing.
This is after the notorious missing new mail sound bug that was fixed an update or two ago.
Nothing funny about my configuration, I have two accounts, Mobile Me and Gmail, the Gmail keeps on asking me for the mailbox password, but that's a problem with Google, no Apple (I hope).
Address Book : I have a friend who since the day I upgraded to Leopard has vanished from my address book. I keep on adding him with the same contact details and a different name, but the next time I sync anything, including Mobile Me, POOF! He's gone again.
For some or other reason, iCal has never been able to pick up his birthday either. But that's been a problem since Tiger.
iTunes : This thing freezes almost daily. The interface turns into a white block on the screen and it's over from there.
My iPods have to be restored on a monthly basis - and they aren't used that often either. There are only two iPods, and iPod classic and a 1st Gen iPod touch both with the latest software.
My question :
Why is all of this happening all of a sudden? This is the exact reason that I own 2 Macs instead of the 15 PCs I could have bought with the money they cost me.
Is Apple crashing? Are we on a fiery path to just another Microsoft "if it can't be good at least make it look good - Bill Gates" company?
I want answers as to what's up with this. It's slowing me down and making me angrier every day.
Message was edited by: Nicholas Lewis

Regardless of keeping your software up to date, it can still be slowly damaged over normal use. Brownouts, power surges, bad RAM (which can result in corrupt data when paging out to disk, though such information is temporary). A frozen app can damage any files it had open, including those belonging to the OS if it uses them to function, by having a write operation stop midway.
I myself just had an issue where Entourage was acting weird, and just in one function. Reapplying the 10.5.6 Combo update resolved the issue by replacing system files with new ones.
I would suggest this.
1) Boot to your OS X installation disk and run a Repair Disk to make sure the drive isn't having issues with a damaged file structure. If you have it, use DiskWarrior as it is better suited to this task.
2) Do an Archive and Install of the OS from your original disks. Then apply the 10.5.6 Combo Update.

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    Important: Information about products not manufactured by Apple is provided for information purposes only and does not constitute Apple’s recommendation or endorsement. Please contact the vendor for additional information.
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    tt2

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