Summing up: between the cost to upgrade, the clunky interface, and all it's doing is updating the one or two road revisions in your area: fugeaboutit.
If I walked into CIA headquarters in Langley and asked them to reveal to me their biggest and most closely guarded secret, their reaction would not be as mysterious as when I ask my Toyota dealership about any kind of software update.
The 2005 nav had a great feature thats been lost. It would tell you the street address of your current location just by pressing the nav button on the steering wheel. Handy if you can get to the approximate location by yourself. Saves you from having to take your eyes off the road long enough to look for numbers. I mainly used it in this mode. The gen 4 has an info button that will tell you what street your on. Not very handy.
You can buy latest nav software on micro SD that goes into entune system for about $120 here's a link.