Just have a gut feeling that VZW Lollipop for the Moto X may not happen until early 2015. Also think that VZW's favorite pet Turbo will get it first, since they're doing everything possible to funnel Motorola buyers to that device. Happy to be wrong on both counts.
My gut feeling is the Moto X will get it before the Turbo, since the Turbo appears to come with more Verizon-branded software than the X does. Verizon was pretty quick to bring KitKat to the 2013 Moto X, and it won't surprise me if they beat AT&T to it again with Lollipop.
On another note, when I updated my 2013 Moto X to KitKat, I did a system cache wipe, and I never had any problems. I intend to do the same with Lollipop, but if a factory reset is necessary, I'm prepared for that too. Regardless, I never felt my 2013 Moto X had a "messy" installation of KitKat because it shipped with Jelly Bean - particularly since the X is pretty darned close to stock Android. I figure with the update to Lollipop my 2014 Moto X will do just fine. By the time AT&T rolls it out, some of the earliest bugs will likely be worked out anyway.