I would. I have a GalaxyTab 10 (the abandoned Google I/O edition) still running Honeycomb that I would happily pay $10 to easily update it to something vaguely more modern. It's been useless for years, not because the hardware is bad, but the software is useless. I still can't figure out how to get something more modern on it. It's been sitting in a drawer (plugged in, oddly) collecting dust forever.
* Care about the Android version on their devices
* Would pay reasonable rates
* Stick with an older phone / don't buy Nexuses
I think the real problem is that it is just turning out to be difficult to make a silky smooth upgrade process, the kind that is consumer-friendly enough to create a mass market. It all fundamentally starts with "hack the device" and most people can't. Maybe it's just a really hard problem because it varies from device to device and base OS version to base OS version.
You might have specific usage patterns where shows but I would say that there's anything wrong with Honeycomb but, rather, that the major problem is that the hardware itself doesn't really stretch enough to run newer Androids or newer websites/applications. I'd just keep the less resource-hungry Honeycomb installed until the hardware can no longer do modern content.
* add products/referral links to os search results (like ubuntu lenses)
* add ads to the base operating system (like kindle's sponsored homescreen)
* sell spots for default search providers (like bing for siri)
And you target old phones by providing them with an upgrade path to cyanogen mod based on a more modern android version. Many devices are technically fully capable of running modern android versions but have been abandoned by their manufacturers.
They seemed to be considering partnering with advertisers to integrate ads into the base OS. Question is, who would voluntarily sign up for such a thing?