wrote:
- I don't just want an entry-level
headset that I'll want to replace before long.


You WONT replace it.. it will become your PASSENGER headset and the
upgrade will be your PILOT headset.

Try some on..
If the FBO rents em, rent one for a flight or two..
See whats comfortable.
Use what works

I recommend gel seals (an option on many, or at least an upgrade you can
do yourself on many)... and ANR.. if you cant afford it right off the
bat, then get a headset that is compatible with aftermarket ANR upgrades
and either do it yourself or have it done.. truth is.. end the end the
cost is the same as if you had bought it with ANR..

Comfortable.
Gel Seals
ANR..

And stick with a major name brand.. doesn't have to be the most
expensive.. but still..

Just my 2 cents.
Dave