I’ve been in the process of figuring out how to synchronize my two desktops and my laptops. Synching files is pretty easy, as there are many tools out there that can do that. Synching Outlook, on the other hand, took a lot more effort.
Since I didn’t want to set up an exchange server, I was stuck using a third party tool to keep things up to date. In the process of my searching I found OsaSync. It wasn’t cheap, $99 for 3 computers, but it had a trial, so I downloaded that.
Configuring it took a while, as I have a 900mb PST, and it had to index everything. However, once it was done, it seamlessly handled synchronizing all my emails, contacts, tasks, and calendar items. After the initial sync is done, it checks the other systems every 15 min or so, and updates them.
So far, it seems to be pretty bug-free, only annoying thing I’ve noticed is that it doesn’t seem to recognize a shift-delete as a real delete, and synchs the email anyway. All that means is that you have to delete the email and remove it from the deleted items rather than just shift-deleting it.
Highly recommended, you can get it here.