This is sort of freaky. Believe it or not we had a conversation on this at my regular game yesterday. I am a chip geek and am trying to educate my friends and bring them into the light in regards to chips, especially the virtues of owning and using quality chips.
Basically, I think it's just comes down to a matter of personal preference (or level of OCD you have

).
This thread piqued my curiosity so I checked a lot of my chips (real casinos and those available to the public) and the majority have randomly oriented inlays or designs. All the clays I have (Paulson H&C and house mold) are random. Many of my ceramics are coin aligned but smoe are random are random.
Whats interesting is the cheaper the chip (i.e. pre-labeled composite chips for the home market) the more they are made with aligned labels (either coin or non-coin aligned).
I have a set of labeled Bees and I prefer a coin labeled chip as in your second example. From what I have observed (myself and my players) the normal tendency is to turn a chip over vertically. Normally a chip was handled with one hand and flipping vertically is a more natural (or say ergonomic) motion. Even if using both hands the tendency was to hold the chip with one while turning it vertically with the other so the effect was the same.
If you do this with a chip labeled like you show in the first example you start with one label in the correct position and when flipped it's upside down. Personally, this would drive me nuts (not that I'm not already

).
When I labeled mine I found it easiest to start the first label with it aligned to an edge spot, flipping it vertically and putting the other one on. FWIW, It went pretty quick and smooth for me this way.
Sorry ablout rambling on.
Ranman