Do I Need To Buy Two Software Upgrades For Two C330 Garmin Gps Units, Or Will One Work On Both Units?

You need to buy two. Garmin Upgrades are licensed per serial number. In North America, at least, you actually have to order two media kits as the license is included in the package.
I just went through this with a a collection of Garmins. The postman delivered an armful of packages.

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