I actually have a formal methodology for how I engage with software/hardware from a FOSS perspective:

Embrace, Subvert, Accept.

For any task I do currently or want to do, I apply this process:

I first try to find and use any FOSS software/hardware that does that thing well enough to use entirely. (Embrace)

If there isn't a FOSS solution that exists or does essential things I need, then I use a proprietary technology in a subversive way to do it. So cracked copies, jail broken or otherwise hacked hardware, or using the proprietary service through an unofficial/unapproved 3rd party app. (Subvert)

If I can't do that either, but the task/need is absolutely critical, only then do I accept using proprietary and unmodified software/hardware. (Accept)

This method has worked pretty great for me. Now about 3 years after starting my FOSS journey, I have almost no software/hardware I use that is in that third category. Basically everything I use is FOSS, hacked, cracked, modded, or runs on platforms that are, and I enjoy tech and computing more than I ever have :)