I have been using (wrestling with, really) gsyncit for about 2 months. I have Outlook 2010 on an Exchange server at my work, and I send my Contacts and Calendar to Google and my Tasks to Toodledo so that I can sync everything up to my iPad and iPhone.
Comments regarding Calendar and Contacts are below, if anyone is interested, so I'll jump straight to my experiences with Outlook Tasks and Toodledo.
This has been so problematic that I have stopped using it for tasks and reverted to using the Toodledo website directly. Repeating tasks were reset to today's date (recent updates claim to have fixed this but I'm still having issues). Even though I set Toodledo as the primary, gsyncit kept letting Outlook tasks overwrite Toodledo tasks. I was constantly having to monitor the syncs for minor strangeness during synchronization. Finally, when Outlook/gsyncit started deleting chunks of still-active tasks in Toodledo, I called it quits. I was spending too much time managing just managing the system and data, and not enough time doing the stuff on my action list.
Bottom line: I looked at several of the solutions available, and gsyncit appeared to have exactly what I needed, but it still seems rather buggy for my situation.
Calendar works great. Contacts works so-so -- on my devices most of my 500+ contacts' address formats get mangled due to some U.S. vs. non-U.S. address formatting issue (could be due to my European employer's default Exchange settings, who knows). Frustrating for detail types like me (is anal-retentive hyphenated? let's find out) but all the data is still there, just not pretty.
@Kurt, since you've switched away from OL Tasks to the TD website, you might want to take a look at TaskUnifier. It would give you a desktop app to to manage your tasks that will sync with TD but still be available if you have no Internet connection. The developer is very responsive & hangs out here a lot! See the TaskUnifier: Multiplatform topic in this forum...