bit late to the game, but I've seen many companies that no longer exists and pretty much share a similar story.
there is 1 developer, isn't 100% dedicated. has other interests and hobbies. few years into it, loses focus, chases tails, loses interest as it's still working. support fades, links no longer work, website starts failing. boom! gone....
Same scenario can be seen in mobile phone app developers as well. mind you that most software has millions if not thousands of downloads, in comparison...
Also, there are new controllers, new hard disks, etc. that, I don't know the programming of DrivePool, but just like everything else, would have to support new hardware and any keep up-to-date with changes to Windows, Linux, etc..
So, I think it is a very valid concern.