Remember not to confuse Ram/FCA with Harman International. (used to be Harmon Kardon, but that name is only used for audio equipment, now)
Harman is the company that supplies car audio equipment to most of the industry.
This "system" is composed of more than just the radio. Speakers and one amp are from Alpine. Hamon provides the computer, radio, and some controls. GPS is from Garmin. The rest is provided by Uconnect, along with some integration. The big difference here is that the system is provided by a lot of different companies. It's not the same as a single smartphone, where chips were supplied to the smartphone manufacturer who puts them together and writes/controls all the software. In this case, each component is made by different companies. The car radio is not made by UConnect, it's just intregrated with control software. Upgrades come from Harman. Doesn't mean it's not possible to do things, but each company is developing its own component and upgrades, on its own schedule. There is no single company doing it all. Uconnect partners with them, and with Ram. The various components have years of upgrades to them, but getting them all on a single cycle is the real issue.
So far, Uconnect software updates are free. But if you're going to add new features like GPS, that's a different story. Smartphones are currently the only commercial industry where new features are "free" and that's because they're not, really. Each new feature on a smartphone leads to more use of the phone, increased data plan use/size, increased advertising, increased data collection on customers, or another profit to the company providing the app/feature. In every other industry, adding a feature costs up-front money. You don't get bigger tires or fancier wheels for free. Cell phones are more insidious.
As far as built-in-obsolescence, that's actually a planned feature in the cell phone world, too. Cell phone contracts last only a couple of years. There are perhaps 100-150 different cell phone manufacturers around the world today. Most cellular phones made have no software upgrade options. Many of them were designed for single versions of their os, and upgrades can brick them, or make them so slow as to be unusable. And let's not forget there are still nearly 50 models of non-smart cellphones. The cell phones people buy in the US are mostly on carrier contracts through Verizon, ATT, or similar provider. People get those phones, swap them out as soon as the contract is done for a new "free" phone. That's a planned obsolescence to get new phones sold on more expensive data contracts and guarantee longer service. In the big picture, it's no different from vehicles.
As for the folks in Canada, so sorry. Uconnect isn't available in Canada because it's not compatible with Canadian cellular infrastructure. Plus, there are some other issues, apparently. Here's the UConnect official statement:
NOTE for CANADA: Uconnect Access is not available in Canada nor can it be added at a future point in time. There is no definitive date when Uconnect Access services will be available in Canada. Numerous obstacles currently prevent the Canadian launch of Uconnect Access including availability of the underlying cellular technology in Canada.