Jordan,
I also had a stricture in my esophagus. I had it dilated 2 or 3 times...I don't even remember. The procedure for me was quite easy. It really is just an endoscopy where they put you under, the doctor sticks a device down there and, if everything works as planned, opens the stricture.
It worked wonders for me. I went from not being able to swallow anything but liquids to being able to eventually eat most anything. I felt little or no pain after the procedure. In fact they give you Versed which causes you not to remember anything, and I was usually a bit goofy on the ride home.
I hope that it works as well for you. It is an easy procedure and nothing to fear.
Best of luck,
Danny G.