Dr. McGinn told me that dilating for the first month wouldn't be too bad, but after that, it would become quite painful for a while.
Like everything else she told me, she was right. The ring of scar tissue and the new area would work to "heal itself" up and dilating would become extremely difficult and painful. Oh, my, that was an understatement! I cried like a little girl when first inserting the dilating stent, it hurt so bad.
It seems like what you describe would be completely normal. This period lasted a few months and slowly began to get easier. I think that it finally became much easier around 6 months or so. Around 8 months, I seem to have entered a new state where dilating is suddenly pretty easy and getting the stent in to full depth is only 10 or 15 seconds with very little discomfort at all. What there is goes away in less than a minute.
The stage you're at will have you losing "depth" in theory. In reality, it will most likely show less depth due to the reduction of swelling and it only looks like you've lost depth.
Don't be discouraged over this difficult period. You will get through it and remember that the less you dilate, the more painful it is and the cure to serious dilating pain is to dilate more. The Doctors know what they're doing and healing can be painful, but in the end, it will all be worth it. Healing will go on for a year or possibly even more.