Hey Luke,

Sorry didn't get back to you sooner, thread hasn't had much activity, so I haven't checked it in a week. Glad you are enjoying the app!

I am a fan of the Pens and Celtics, both in their respective playoffs. Pens have advanced, Celtics still trying to advance. Do I understand correctly that once the Penguins second round opponent and schedule are known that it will automatically update and be added to my calendar?
In order to see them on your calendar you will need to update your teams in the app, however starting with v1.1.0 you can turn on automatic updates if you would like. Please see FAQ Updating your Calendar Unnamed Apps for more detail on auto and manual updates.

And if so (or even if not), does the app auto update/delete a game six or seven when a team wins a playoff series in fewer than six or seven games?
Yes, the app will remove game 5/6/7 if the series is over.

Lastly - if I input all my faves now, will those roll over in future NFL, NBA, NHL, MLB seasons when the schedules become available - or will I have to request my team's schedule new every year as each season approaches?
You only need to add them once, after you have added them the app will check the latest version on your local calendar with the version on our servers when it updates(see updating link above). If there is a new version it will make the changes locally to your WebOS calendar. So, when the new NHL schedule comes out for 2011, it will pick up the new version automatically during the next update.

Let me know if you have any more questions!