(To get categories nicely set up like this, follow the advice from Outlook Guru Diane Poremsky at http://www.slipstick.com/outlook/outlook-categories-flags-and-imap-accounts/)
I also find Outlook very satisfying because I can drag messages to appropriate folders, and the folder hierarchy is much easier to manage than in Gmail.
Furthermore, there is a separate page called “tasks” where I can view all my flagged messages at once, grouped either by folder or by category. This makes for a powerful way to implement GTD and Inbox Zero.
So I want the best of both worlds: while at my home office I want the power and features of Outlook, but I want to retain the option of searching and viewing my messages through the Gmail web interface.
You would think this would be simple: just click File -> Add Account and then give the information for Gmail. Unfortunately, there are some details that if you get wrong, will cause a huge amount of frustration.
I set mine up that way and it worked for a while, but it would intermittently not work. One day I had to spend a day working with Outlook while offline. I spent the whole day checking off flags, and moving emails around into various folders. After that day the sync no longer worked.
The Issue
As I found, the Outlook to Gmail IMAP interface can be painfully slow (as described in this video), and in fact apparently can stop working completely, unless you have certain settings correct. You can easily get stuck on "synchronizing subscribed folders" during the Send/Receive step, and Outlook will either take forever or never complete the Send/Receive.
This is the IMAP issue I am referring to:
http://answers.microsoft.com/en-us/office/forum/officeversion_other-outlook/synchronizing-subscribed-folders-issue/ec6835a6-cf06-4f9f-9432-37af831631c4
I paid $100 twice for Microsoft Premium Support, but they were unable to fix the issue.
I also considered just migrating all my Gmail messages into Outlook.com (formerly Hotmail), to take advantage of the fact that this webmail uses the Microsoft-Proprietary ActiveSync protocol, which might not have had the issues that the IMAP protocol has:
http://www.labnol.org/internet/import-gmail-into-outlook/24518/
http://www.pcworld.com/article/2011519/how-to-move-from-gmail-to-outlook-com.html
The old tool used for this purpose was called “TrueSwitch” but it is no longer supported, as even Google itself points out:
http://www.dataliberation.org/google/gmail
Another option was to use the Windows Live Essentials to import/export mail messages.
Fortunately I found the solution described below before taking the drastic step of migrating away from Gmail.
The Solution
The only solution that I found was:
(1) Create New Profile
If your Outlook sync is not working, I recommend you first create a totally new profile and download the messages from the Gmail server again. I know this is a giant pain if you have gigabytes of data, but on a strong connection it should only take a couple of hours, and for me it was the only way to ensure that the other steps below actually worked.
(2) Modify “Send/Receive Groups” settings
Run Outlook /profiles and select your new profile. Then Press Ctrl-Alt-S to visit “Send/Receive Groups”. Alternatively you can access it from the Ribbon here: