You don't need an AI, "just" increased tracking and data analysis to improve troubleshooting, like MS and Google do. Unfortunately, Ubuntu caters to a community that is very much adversed to the idea.
Another alternative is to dramatically restrict support for hardware configurations, like Apple does, and let the community deal with the rest. There would be some backlash but it probably wouldn't be lethal.
To be honest I don't think support is the problem anyway. The problem is that monetization channels are not materializing at the necessary volumes. RedHat "is" Linux in the enterprise datacentre, where the big money is. Ubuntu seems to rule the virtual-machine arena, which is a world of cheapskate corner-cutting startups; and personal desktops, which are fully commoditized. Their saas offerings have failed, and there are limits to what they can extract from iaas providers. Where can they find real money?
If I were Shuttleworth I'd try again with integrated services, but by acquisition and with better targeting. Ubuntu users are geeks, they won't pay you to save a few holiday pics. Buy and integrate dev-oriented services like spideroak and tarsnap; build some revenue-generating agreement with Jetbrains, Microsoft, Oracle etc to integrate their tools on Ubuntu; build a real appstore (i think they are working on something like that). This stuff won't generate bazillion dollars, but could create the space to find that one or two killer features that people will pay good money for.