Yeah, could just be that your ears don't like those cans; try a different pair and see. Just this quack's opinion...

I agree that they're sort of a nuisance. I often take mine off for a few minutes, if the situation allows... I've realized that the noise inside the plane isn't all that bad (although it sure seems that way when you first take off the headset!), but over time, it'll take its toll. And I have yet to hear a speaker in a Cessna that I could stand to use much for communications...

No doubt the range decreases with age (damn things just wear out, i guess) but if you're careful, you'll be able to avoid toting a big ear-horn around for a long time.
Last time I was tested I did OK up at the top of the scale, which is amazing considering I've worked in construction, a nightclub, recording studios, and played drums in rock bands for years, often foolishly not using any ear protection (ah, youth!)... but I do have a bit of tinnitis ("The bells! The bells! Sanctuary!"), and sometimes loud music will make my left ear do some very odd things (used to keep the monitor wedge on a box right by my left ear when playing drums- stupid!). Fortunately, it's not intrusive (yet), and definitely is associated with stress, fatigue, and the occasional sinus-blockage.
As for pinching and blowing (sounds dirty, doesn't it?), absolutely must be done gently, better three or four gentle attempts than one big blast; and it works well for me to do this
before I feel any discomfort- actually seems to help prevent it.
On the few SCUBA dives I've done, the rule was to more or less continuously "clear" on the way down as a preventative measure- very different pressure differential than climbing to 1000-2000 feet in flight, but logic dictates the same rule applies, to a lesser degree. So in flight, I'll usually do it a couple of times whenever I'm going up, and often when descending, especially if I've been cruising for a long time.
On flights past 5000 I almost always sense the need to clear my ears at some point (although once in a while, I'll feel the pressure climbing or descending at much lower altitudes)... but yes, very gently.