Jeff,
Just saw first post question.
Cuffitis can be diagnosed by scope or simple anal finger exam. There are often bumps in the anal canal when performing the anal exam. I had severe anal irritation and burning for many months (no blood) after takedown that it thought was just normal recovery until I had a full scope under anesthesia. I also experience more of the pressure sensation you describe when the cuffitis is active.
I am at two years and take Canasa daily for chronic cuffitis. It is not the optimal solution but without this I would need pouch advancement surgery for that very tiny anal transitional zone area that gives me so much discomfort.
The scope or simple in office anal exam should give you answers but if the pain is internal and not external, your GI may be able to prescribe something to help. If not, warm baths will help with the pain and irritation until you can be seen. I also found calmol (hope spelled right) suppositories that you can get OTC at pharmacy helpful as long as GI agrees. Good luck.