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.