Just got a "new" Moto X 2013. Should I upgrade from Kit Kat?

I'm limited to what ROMS I can flash if I leave it on Kit Kat right? I can only install Kit Kat roms? So if I want Lollipop roms, I have to do the OTA official software update to Lollipop?

Or does it not matter and I can just flash whatever version I want no matter what OS is currently installed?

Thanks!

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