Depends on Planned Activities
What I carry depends on the activities I am leaving the home for, if I am going to be in a classroom, or office environment all day, I usually carry a S&W Model 42 in a pocket holster. Bigger pistols for the drive to and from are locked in box in the trunk of the car when it's parked, but handy for wearing and keeping close while driving in traffic or in less desirable areas of the city.
Going out to dinner with the family, I'll wear either my Sig 229r, S&W 4006, or Kimber CDP in a IWB holster.
Going out on my own to run errands, then it's either a Python 4", S&W 686 3", S&W 29 4" or S&W 629 2" in IWB holsters.
Around the house, I tend to either wear the Sig 229r or a Colt Cobra (2nd Gen.) in OWB holsters.
I really haven't settled down to carrying just one all the time. I prefer the .357 wheel guns, but in crowded places or out with the family I feel better with a higher capacity weapon in a .40 or larger caliber.
I really hate vacations, on these I have the .357 S&W 686 in the center console and wear the S&W 4006 in an IWB holster. I take the S&W Model 42 along for those occasional times when a weapon in a holster just doesn't fit and I want something in a pocket holster.
Course, every time I carry, I always have an extra mag or 2 speed-loaders.
Someday I hope to settle down to a one and only, but after the past 3 years, I think it's going to be some time yet...