Is the latest version on the Garmin site the 2008 or the 2009 version? If it's not 2009, does anyone know when it will come out? How often does Garmin update this software?

Not sure how old this post is, but the latest map update is 2010.10. That is for lifetime map purchasers. For one-time map purchasers, it would be just 2010. Lifetime purchasers can usually get 4 updates per year for the life of their device (cost about $110.00). One-time updates usually run about $60.00, so the lifetime purchase is really a bargain. For one-time map purchasers, the mapsets usually come out each year in the April - June timeframe.

Joel