I was never inconvenienced by being on the Kindle ecosystem, since anything I would like is there, and possibly for a lower price than the rest. Plus, the reader syncs to the cloud, and if I'm stuck waiting somewhere for an appointment, I can just continue reading on my phone.
Using Calibre and de-drm-ing books is way more of an inconvenience. If anything ever happens and Amazon wipes out my library, I would just feel like I could get an already de-drm-ed "backup" from someone else, to the same effect as doing the process myself