“Pressure” is typical. “Discomfort” is typical. If you don’t have an underlying condition like a sinus infection, “pain” is not typical. You might want to talk to an ENT.

I’m a balloon pilot. My ears will typically first equalize about 500 feet above ground level. I’ll occasionally hear small little “farts” as the pressure changes, but I rarely feel anything more than slight pressure.

but multiple times I’ve gone from sea level to between 5k and 10k feet, and when my ear pressure equalize, it is often quite painful for minutes.

If your ears aren’t equalizing until a 5k ascent, that’s approximately 2psi pressure differential. I can see how that would be quite painful.

If your ears won’t clear at all, yes, you’d have a problem. But, you’re indicating your ears do eventually equalize. You won’t experience more pain than what you already do.

Even though there is an 8psi difference between cabin and atmospheric pressure, your sinuses apparently start “leaking” at a 2psi differential; they won’t build up an 8psi difference across your eardrums.

You might try a nasal/sinus decongestant before an ascent. Pseudoephedrine works best for me, but it tends to make my head swim. Oxymetazoline nasal spray works well, but I get terrible rebound congestion from it. Phenylephrine pills do nothing, but phenylephrine nasal spray (“4-Way”) works very well for me.