Let me update my experience. I got two sets made by Westone a few months back. I got a pair for sleeping and one for wearing while riding, the 4RTs. I was not happy with the ones I had made, the seal kept breaking and they didn't block as much noise as I expected. I had three months during which to get them remade. My problem was made worse by the fact I have very small ear canals.
I went back and we made new impressions. In reading, I learned that the recommendation for hearing protection ear molds, was to have the impression made with the open mouth bite block method. Basically you have your mouth wide open and they give you a bite block to put between your teeth in order to keep your mouth open properly.
My original impressions were made with the closed mouth, chewing method. I was told to chew a few times and move my jaw a bit to help make them more comfortable.
My ear doctor didn't have bite blocks but we did it without them, I just held my mouth open wide and held it there. The difference was very noticeable. The new ear molds are comfortable but seal very well and block more sound. They are fantastic. I also got another full shell pair made on my second trip and they work very nicely although I don't use them often.
The impression is the most important part of the process. I highly recommend going to an ear doctor. If they don't work right, they will do it over for you. They will also better be able to make the impression without harming your ear. Yes it can happen.
Mine only cost $90 per pair, including the impressions. She also put me in a sound booth to check to be sure I was getting good attenuation of sound. If I have any comfort issues, I can go back and she will file down any spots that cause problems or pain or do what it takes to get it right.
For $90, it was money well spent. I wear the sleeping ear plugs often, on planes, and I fly on average once a week, and while sleeping. They are extremely comfortable, no more pain. I can wear them all day with no discomfort.