My childhood was riddled with countless ear infections and I wear hearing aids today as a result. I still get them, but am sometimes required to fly in the midst of one.

Usually after a day on antibiotics my symtoms are much better and the inflammation is down. If delaying your flight isn't an option, I think your plan sounds like you have thought of everything.

The only other recommendation I would have is Auro. It's a homeopathic ear treatment found at most department stores for about $6. It is supposed to work on ear pain. I don't get a lot of pain relief from it, but I do find that the oil does "cool off" my ears and the drops help buffer some of the noise, which helps me sleep.

Good luck!