For the pressure on the temples, I noticed that when I wore a bandana or a baseball cap, the pressure wasn't as bad and I didn't end up with a headache after the show. My physiotherapist thinks it might have to do with the band sort of spreading out the pressure. I don't know if this is true or if it works for others, but that's what works for me when it comes to the mechanics of wearing a headset. Plus, if anyone in the booth is bugging me, that night I grab the bandana from my hockey bag and threaten to wear that one in the booth!
If it's a volume thing, we are kinda stuck in this industry. If you have to hear it and you can't, make it louder. For everyone out there I recommend getting a baseline hearing test done right away. Keep that record on file. If you are ever involved in an incident that causes hearing damage or loss, you have on file a record of what your hearing used to be and may be eligble for compensation. At least that's how it works in Canada. Even if you're place of residence doesn't do this, it's always good to have it checked considering how important it is to our jobs.