A few personal observations:
- ANR is, in the words of Richard Collins, the greatest thing since seat cushions when it comes to comfort in GA aircraft. It has also improved tons over the years.
- before you spend any "medium" amount of money on a low-end ANR headset, try a Bose A20 or Lightspeed Zulu.2 or something in that league. In an airplane, if at all possible. Only after that make a decision how much more quiet is worth to you.
-I have never understood why so often students are told to start out with crappy headsets. Many PPLers will never again fly as much in as short a time as during their training. Why suffer through it?
- it's not that some headsets don't match. It's that some intercoms are total cr*p. A good intercom should handle any mix.
IMHO, friends don't let friends use passive headsets. ;-)