Good question for me, since I'm getting back into shooting and am trying to decide where to start:
Guns I'm looking at:
Glock 23, which is what I'd like to use to get into IDPA.
Glock 27, although I'm tempted by the Ruger and Taurus .380s: I don't know that I'll need to carry much, but I'd carry more if it was a fairly light and small piece even though the calibers don't really compare.
A Taurus 65 B4 or a 44 Tracker 4B for backwoods use, still deciding on the caliber.
A Beretta 92 or a S&W 5906, I've owned both in the past and loved them, fun guns to shoot and 9mm is comparatively cheap for practice ammo. The fact that the 5906 is discontinued is swaying me toward the Beretta.
A .22LR, still trying to decide on a Taurus 5" barrel revolver or one of the inexpensive S&W pistols, for regular (and cheap) practice.