Tony Mayer at JM and I had this discussion earlier this week. While I have boxes and boxes of various holsters, initially I assumed one appendix holster for a particular gun was all I needed. I have come to realize, that just as I have different purpose OWB holsters, I have different appendix holsters for different purposes.
The conundrum is that optimal speed, concealment, muzzle orientation and retention likely do not ALL come in the same appendix holster. Take speed for example -- for me, best speed comes from a high ride, with the butt not so radically tucked. Concealment comes from a lower ride, that might whack my knuckles on the draw, with the butt wedged as tight as possible against me. Best retention is slower and may come from leather. A big pad that averts the muzzle as far from your body as possible, can make getting the butt harder, especially with a smaller pistol.
Lately, I have settled on a two holster strategy. A JM "George" for most of my needs, and a Universal with a clip for lower ride, better concealment, and easy on and off as I switch clothing or go to USPSA practice gear.
What are your strategies?