Neil is tough to peg. He was "notoriously" pro-Reagan in the early 80's, and also made some unsympathetic AIDS remarks. He was duly slapped down hard by the PC police, and "saw the error of his ways." The Rolling Stone/Hollywood music establishment has never tolerated any dissent from it's subjects.
A de facto blacklist also exists in the British music scene: Any expression of support for Thatcher or Tories will effectively kill your career, thanks to the powerful music press over there.
Neil is his own man. As MTV was taking over music and Phil Collins and Eric Clapton were being bought and paid for by a beer company, Neil wrote "This Note's for You" with its blatantly anti-corporate sponsorship lyrics and filmed a video mocking Clapton, Michael Jackson, etc. At first MTV tried to reject it, then played it, then named it the video of the year!
When asked by an enviro-whacko interviewer in the early '70's where he would be when the revolution against technology and capitalismbegan, Neil answered "on my ranch with my guns."