Edit years later:
Using KeepOutlookRunning mentioned in the duplicate question: http://superuser.com/a/275244/49695
Finally figured out a working solution that doesn't involve installing something I have to pay for... I've been trying to figure this one out for weeks before I really put too much time into it today:
# Start outlook if not running
if (Get-Process "OUTLOOK")
Invoke-Item "C:\Program Files\Microsoft Office\Office14\OUTLOOK.EXE"
Setup a task scheduler that runs every 5 minutes. If outlook is found, empty part is run... else, Invoke-Item runs Outlook.
To enable running of Powershell Scripts... Enable running of locally created scripts (foreign scripts must be signed by a trusted source):
run Powershell as administrator
Bam. I know I'm not the one with this problem... and don't wish to spend $60 on a solution for something so simple. I'm not cheap, but I'd rather spend that money on my girlfriend :)