Open at Login Not Reliable

Freshly installed (not upgraded) Mountain Lion, OSX 10.8, all updates installed. I'm the admin of the computer.
I have several items that I want to Open at Login. I right click their icon on the dock, go to Options, and then Open at Login. I only have a few of them, such as Outlook, Messages, and Firefox.
After a complete restart, those items only Open at Login about 50% of the time. The rest of the time, they just sit there, unopened, no matter how long I wait.
Note that I am NOT talking about the "Reopen windows when logging back in" checkbox when I restart the computer using the Apple menu. I have that option unchecked (and have always had it unchecked) and it performs like it's supposed to. It doesn't re-open apps or their windows, which is what I want, and this checkbox shouldn't control the "Open at Login" dock / app setting anyway.
The morning routine is the same. I power off my computer the day before, come in during the next morning, turn it back on, wait for the login screen and I click on my name and put in my password.
I like to log into my computer and get some coffee while it loads my apps and starts my Outlook mailbox sync, load up my Firefox tabs, etc. It's aggravating to come back to my computer 5 minutes later and see that none of the apps I told to Open at Login actually opened.
I absolutely never had this problem with Lion or Snow Leopard. It worked 100% of the time with those operating systems.
How do I fix this on Mountain Lion?

I don't need to re-arrange them, but I could see it being a useful troubleshooting step if only one app was Opening at Login but the rest were not.
Sadly this is not the case anyway, as it's an all-or-nothing kind of problem. Either all the apps are loading on a login, or none of them are. I'll have to restart the computer a few more times now that I did a permission repair and see if that resolved anything.

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