It definitely is an individual thing. I don't knock those who carry differently depending on their perception of how things will be so long as they carry period.
Personally I carry in the same place every time and all the time. From the first moment I'm dressed I'm carrying and carry till I undress to go to bed. That said I DO change my choice of guns to carry depending on what I'm wearing. In warm weather I go with a smaller gun for easier concealment. In cold weather I've got my 1911 on me all the time.
My reasoning is that I train myself to draw and shoot from the 3 and 4 o'clock positions the most. Every month I put 750 or so rounds through my guns drawing from those positions. I probably put another 250 rounds into my guns drawing from the 9 or 10 o'clock position (cross draw). So then carry in the position(s) I practice most in. I see no reason to stick the gun somewhere else and confuse my muscle memory.
This is who we are, what we do.