I have a drawer full of holsters, much like most prople that carry on their person.
I have never carried SOB. The thought of sitting and having to lean back against the gun just never appealed to me. But until recently, I have been carrying a full size 1911 and the thing is a brick! Maybe a different gun would make SOB carry more practical.
I have found that carrying at the 3:30 to 4:00 position to be the most comfortable for me. I most often use a IWB kydex/leather holster (Concealment Solutions in Orem) and can wear it all day without much discomfort. In the colder months, I will carry OWB in a cheap little slider that keeps it tight against my hip.
I have had to draw my gun one time on a person with a knife whom apparently had too much to drink and thought it was a good idea to get behind the wheel of his truck. It was a natuaral and automatic draw, and I wasn't really concious of doing it until I had the gun in my hand. One thing I have come to appreciate about the 4:00 carry, it is reassuring to be able to feel and shield the gun with your arm and elbow. One thing you have to keep in consideration is how you plan on keeping the gun secure against your body in the likely event that an altercation becomes up close and personal. I don't think I would feel that the gun would be as secure in the SOB position.