Thanks for the post and yes you're correct, I wrote the paths incorrectly in my original post; it should have been C:\Program Files (x86) in both lines. I had this in my command and it isn't the issue. I have the Organization field filled with case-sensitivity to match exactly what comes up when configuring manually.
I've added the /l switch and the log file don't have a whole to say:
09:35:22| Info| === Microsoft Dynamics CRM for Outlook Configuration Wizard logging started: 24/09/2013 9:35:22 AM ===
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.ClientConfig.Initialize
09:35:22| Info| Client Configuration Wizard Version : 5.0.9690.3448
09:35:22| Info| Client Configuration Wizard LanguageID : 1033
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.Validator.IsOutlookInitialized
09:35:22| Info| Query all rows in profile table
09:35:22| Info| Outlook is initialized
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.Validator.IsOutlookInitialized
09:35:22| Info| Client Configuration Wizard Running Mode : Normal
09:35:22| Info| Configuration file Type : OnPremise.
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.MainForm.MainForm
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.ConfigInfo.ConfigInfo
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.OutlookCRMDatastoreInstaller.GetAllCRMOrgsInOutlookProfile
09:35:22| Info| Logon mapi store
09:35:22| Info| Logon admin service
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.OutlookCRMDatastoreInstaller.GetServiceIds
09:35:22| Info| Query all rows in msg service table
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.OutlookCRMDatastoreInstaller.GetServiceIds
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.ConfigInfo.CleanUpDatastoreIfNeeded
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.ConfigInfo.CleanUpDatastoreIfNeeded
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.ConfigInfo.ConfigInfo
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.MainForm.MainForm
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.MainForm.MainForm_Shown
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.MainForm.AddServer
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.ServerForm.ServerForm
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.ServerForm.ServerForm
09:35:22|Verbose| Method entry: Microsoft.Crm.Application.Outlook.Config.ServerForm.SetUIData
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.ServerForm.LoadAvailableUrls
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.ServerForm.LoadAvailableUrls
09:35:22|Verbose| Method exit: Microsoft.Crm.Application.Outlook.Config.ServerForm.SetUIData