The fill station should be well maintained and clean but it isn’t necessary for it to be all shiny and new – most of this stuff is pretty heavy duty equipment and it isn’t uncommon for parts of it to be old. What matters most is the result which is why reading the test report is so important, though I personally avoid places that still wet-fill, no matter what their test reports say. If they don't check your C-card and look for hydro dates and VIP EOI stickers, you know they are sloppy with protocols and you should be nervous about what they're going to put inside your cylinder. Likewise, if they sell anything other than plain old air they should use a fill log, have a suitable analyzer available and insist that you use it when you pick up your fills.
If you're interested in this stuff, I recommend the previously mentioned
Oxygen Hacker's Companion book and the
ANDI Oxygen Handling and Gas Blending course student manual.