>A lot of my friends use Linux and tell me that if I spend the right amount of time tinkering with it -- making it mine -- I'd reap the benefits of a bespoke OS, just like slipping on a suit that's tailored just for me.

If you do things like change your keyboard layout to Dvorak/Colemak, go for it. It really is a more productive environment once you're used to it, but the trade-offs are similar. Yes, you can tailor everything the way you want, but it can be very time consuming and you lose out on the ability of having anybody else know how to use your computer.

Anecdote: I came from Arch Linux to OSX. I find the tight integration between hardware and software on my 2012 Air to be a breathe of fresh air from the hacking it takes to get basic hardware support sometimes on Linux. IMO, tools like vagrant make native OS matter much less nowadays as long as you are working in some kind of *nix environment.