1) I live in a remote place. Getting stuff shipped here is very hard and finding "Ubuntu-friendly hardware" is simply not an easy option, at all. I find it odd that Ubuntu is purportedly an answer for those who live in rural or remote areas, yet those are the areas where it can be extremely difficult, or expensive, to get specialized Linux-friendly hardware.
2) I've spent lots of time digging through documentation, reading about packages and messing with various pieces of Linux over the years. I am constantly SSHing around to various boxes for development and administration. I'm no stranger to config files, man pages, or Linux.
3) As I grow older, I'm finding that my time is definitely equatable to money. This is especially true as a freelancer. There was absolutely a thorough amount of "is this worth it" over the course of months, if not years, before taking the plunge.
Ultimately: the time and frustration investment reached a threshold where throwing money at the solution became a viable and intelligent alternative for me. I'm not advocating that this decision is for everyone, only telling the story about how it became the decision I made.