Personally I didn't do the $500 upgrade but I dont listen to the radio much. $500 is a lot of money just to listen to the radio, that could be 4 years of paid Spotify premium for the same price.
It sounds like you do listen to it a lot and it might be worth the extra money just to have the snappy/ease of use of tuning the radio instead of loading the streaming and buffering and loading of the online radio equivalent.
If I were you I would try out the "free" streaming options and then decide if it is too much of a hassle. It's the same $500 if you do the upgrade at the same time or not ....but.... they may no longer offer the upgrade to the radio service in the future.