I have been under about 7 times already and I still don't like it. I am a bundle of nerves before any surgical procedure. The truth is there is very little risk of dying in surgery and if you want, you can reduce the risk even more by selecting a surgeon who operates out of a major medical center where any support you might need is available. Yes, the cost might be a bit higher but the peace of mind will be worth it.
As for dilation, one or two missed sessions isn't the end of the world and after the first year or two, missed sessions are even less critical. The first month out of the hospital, I was supposed dilate 3 times a day but (long story) because of exhaustion I could only manage 2 a day. Fortunately it didn't cause a problem. After about 20 years of the once a week dilation, I was a bad girl and went 10 years without dilation. The first couple of months when I went back to dilation, the were well a bit uncomfortable but I was able to use my regular dilator and I still have the depth of about 6 inches.
As for pain, some people feel it more than others. The only pain medication I received was what they gave me while I was in surgery. Had I needed it, morphine was available and I only needed to ask for it. I have seen surgery here in Phoenix and a morphine pump is connected shortly after surgery and you are given a button that allows you to control your dosage. If you feel pain, you only need to press the button and you can request up to the maximum permitted dosage. After a couple of days, the level of pain will drop to the point where mild or no medication is needed.
The decision is yours but in my case, the fear I had to deal with was well worth the price to get my surgery. From the first moment I woke up after surgery, I have never regretted my decision.