Retina, 6864 63 bytes
M!s`"(\\.|[^"])*"?|'.|\d+|\Sms`^'(.)|^"(([^\\"]|\\.)*$)"$1$2"
or
s`\s*((")(\\.|[^"])*(?<-2>")?|'.|\d+|.)\s*$1$2¶\ms`^'(.)"$1"
I think this covers all the funky edge cases, even those not covered by the test cases in the challenge.