When setting up JW!Convo, the first thing you will see after installing the toolbar is a popup asking for a username and password (and a password confimation). I’d recommend NOT using your email account’s password, but something else that you’ll remember. This will provide even better security for your mail.
Once you’ve installed, hit Mass Import and the toolbar will pull a sample of your Inbox and Sent mail (125 mails from each) to give you a glimpse of what JW!Convo can do.
The Gmail-like viewing in Outlook is available either by clicking on a mail in your inbox or Sent mail box and then clicking on View Convo in the tool bar, or by clicking on View List in the look bar and then clicking on an email address in the list. That will bring up the conversation view similar to what you see in Gmail. The big difference is that the mails are shown from the first time you’ve mailed back or forth with someone and then also sorts by Subject on the left hand side.
Let me know what you think. If you have comments or suggestions you can post them here or at http://www.jasonwiener.com/bugs/.