This is what I found for doing it 'on the cheap'. This is not flawless by any means, so please don't do this with your eyes closed ;-) Do pay attention to the warning about uploading duplicate entries in Google.

I specifically did this for migrating data up to Google Apps, but having done similar things for my own personal Google account, I don't believe there's much difference.

I decided to write this up because it still seemed like a largely unanswered question out there. The Mac version of Outlook certainly doesn't make any of this much easier, what with formats like OLM! So much so that there are more than a few vendors of OLM to PST conversion software.

[Oh for those of you wondering why I didn't use the Google Apps Migration tool for Exchange (GAMME), it was because our hosted MS Exchange service only gave us limited access.]

Migrating Contacts:

In Outlook:

1. Go to File -> Export
2. Select the "Contacts to a list (tab-delimited text)" radio button
3. Note where you've saved that file

In Excel:

1. Open Excel, then open the file you saved in the last step
2. Excel will prompt you with the Text Import Wizard. Click through ensuring that Tab is the selected Delimiter.
3. Unfortunately, since the export isn't perfect, it's a good idea to eyeball this list of contacts and ensure that the data appears to be in the right columns. E.g. First names appear in the First Name column, etc.
4. Now save the file as a CSV file: click File -> Save As. Select Comma Separated Values (.csv) as the Format (near the top of that list), and save.
5. Note where you've saved that file.

In Google Apps:

1. Navigate to the Contacts section (either via Gmail) or the top navigation menu bar.
2. Click the More menu (with the down-arrow next to it) and select Import…
3. Use the Choose File button to select the CSV file you saved in the last section, then click Import.

Note: if you need to edit your CSV file and re-import to Google Contacts, it's best to delete all of the contacts from Google before performing the import again. This is because Google doesn't overwrite the original contacts, but creates new contacts, which will create duplicates in most cases.

Migrating Calendar:

In Outlook:

1. Go to Outlook -> Preferences
2. Click Sync Services
3. Check the Calendar box and ensure that your main account is checked under "accounts to sync"
4. Now close that dialog box (red circle)
5. You will get a prompt titled "You have turned on Sync Services". Click OK.

In Calendar:

1. Open Calendar (used to be called iCal)
2. Ensure that your calendar(s) from Outlook are there
3. Right-click on the calendars you want to copy and select Export.
4. Keep or change the name and click Export

In Google Calendar:

1. After logging into your Google Apps account, select Calendar from the top menu
2. Click the drop-down menu next to the gear icon (top right-hand corner) and select Settings
3. Click the Calendars link (top left-hand corner)
4. Now you either create a new calendar or import into the default one that uses your name as the title.
5. Click Import Calendar
6. Browse to the .ics file on your computer which you had previously saved in step #4 above. 6. Select the calendar you want to import into and click Import.
7. You should see that some # of events were processed, and then see those events when you browse back to the main Calendar page.

Hope this helps someone out there!

I have finally found a work-around for this issue. I found on the Microsoft support site.

It basically entails setting up an additional account(for the same email address) without a signature. you then create a rule that moves all incoming mail to the account without a signature and then flip a few toggle switches so that you are not receiving mail twice.