I got used to wearing the bag fairly quickly, although it still is slightly uncomfortable to have the bag and go out to appointments and food shopping. I worry too much that the bag will just detach from the wafer while I'm out. It took me a few weeks to feel comfortable with changing the pouch myself. The visiting nurses have helped immensely.
Sleeping with it isn't so bad; the first couple of weeks it felt uncomfortable to sleep on my sides, but I could sleep OK on my back. Now I can sleep on my sides fine. I wake up at least twice during the night to check the bag, to see if it needs emptying, but I fall back asleep quickly enough.
Words of wisdom: stay hydrated - some foods will make you lose fluids really quick, just make sure you replenish well.
If you find that you empty the bag a lot, ask your doctor if he/she would recommend Metamucil and Immodium.
Bottom line: I would go through the surgery, again, if it meant not having to take steroids and immunosupressants for the rest of my life.
Let me know if you have any more questions.