I have encountered a few places that have contactless terminals where the staff don't even attempt to use it. So far, my local dentist, vet and a few corner shops have had contactless readers but they hide them behind a desk and when asked if they accept Apple Pay or Contactless, I get a blank stare or a no. So I hand them my card and they pull out the terminal which is clearly contactless (I can see the contactless logo on the screen from where I'm standing) and stick the contactless card into the reader.
I feel like the only way to actually use Apple Pay sometimes is to trick people into letting you use it. Sometimes it's not even worth the hassle. I work in retail and when I'm out shopping and want to use Apple Pay, I feel like I'm training members of staff when I have to teach someone else how to use contactless on a terminal. It's not even difficult but some people have no idea.
I get through my transactions much quicker simply by handing people like this my card and letting them insert it into the reader, rather than asking them to hand me the the terminal so I can tap to pay and then get 21 questions of confusion and disbelief.
Contactless and Apple Pay is supposed to be quicker than your traditional chip&pin, but if staff don't know about it, it turns into a painful and slow process. I once went to buy some things from a branch of where I work, not the store I work in, and at the checkout I had to explain to the lady how to take Apple Pay (simple as hitting the card payment button). She kept telling me that because my total was over £30, contactless would not work, I told her that we accept Apple Pay so it doesn't matter. It took a lot of back and forth, eventually I got her to hit the card payment button and she couldn't believe it when the payment went through. She apologised and told me she had no idea phones could do that. I imagine if I wasn't an employee she wouldn't have hit the card payment button.
It's absolutely up to employers to train their staff on Contactless/Apple Pay. Especially Apple Pay as it's newer and a form of payment in and of itself. For smaller businesses, my guess is that some just happen to have a contactless terminal and don't even know or care enough to bother using it.
I've got a couple of Contactless promo t-shirts from a previous retail job a few years back when that company first got contactless terminals, maybe I should start wearing them when I go shopping. You'll see me on the streets with my contactless shirt spotting phone masts waving my phone at terminals