I'm a fan of Volvo of Penrith
No one outside of a Volvo dealer in Aus can do software updates, so in general... it is best that it go back to a dealer once a year
Software update outside of a service is $250 or less, so with the 5 year deal... your paying $250 for a oil change which isn't that horrid....
Anyone can do the oil change who can follow basic directions, BMW's have not had dipsticks on some models for 17 years now...
If you plan to only keep the car for 5 years, the 5 year $2500 plan is not a bad price
If you plan to keep the car over 5 years, then get the 5 year plan and have the oil changed by an Independent at the 6 month mark (between dealer services)