Well, I'd say in 80% of the cases it's appreciated, I think you can tell it if the person is like "oh thank you very much, etc." or more like "ok... thanks". It always depends on the situation.
Usually if I compliment someone to start a conversation it's just what it is: A nice conversation starter and the conversation continues, but it should be honest regardless, because you can tell if someone lies and I'm a pretty bad lier to boot. xD
I remember complimenting the hat of some dude a few months ago but it wasn't honest from my part, I just wanted to talk, he could tell, so the start of the conversation was pretty awkward (but that's my fault).
In the end it didn't matter because we talked about other stuff and it was a cool conversation, but I felt bad afterwards because the start was so awkward, so: never again. (I still cringe thinking about it lol)
Yes, definitely.