This is a bit silly. Some of it doesn't appear to be Americanisms rather than just bad grammar. Others are just words we say differently, like math and maths, or period and full stop. It's just the development of language!
And really, "transportation"?! From the people who say "orientated" rather than "oriented"?
And what's wrong with "train station" (#22)? What else do you call it?
"Gotten" came from here!
I'm not sure "Can I get..." Is 90s New York so much as it's bad manners.
Kiddo says it all the time and it does my head in. A lot of kids say that here and they certainly didn't get it from 90s New York, they weren't even born yet.
I've never heard "winningest" in my life.
"I could care less" is used by the same people who say "irregardless" and "for all intensive purposes". It's not an Americanism!!!