A S&W M442 inside a Milt Sparks Executive's Companion is as comfortable as it gets. If you can tolerate more weight, the S&W M640 (.357 magnum) with the same holster is all day comfortable. With autos I have found the Sig P232 (.380) and Kahr K9 to be extremely comfortable. Note that all four of these handguns have no sharp edges and, except for the Sig, no exposed hammer. The Sig hammer rides low and does not cause discomfort. Without the holster, the M642 with 5 rounds will weigh around 26 ounces, and the Kahr 9 with 7 rounds will weigh in around 32 ounces. A good holster and a good belt helps them ride comfortably all day. The M442 airweight fully loaded will weigh less than 20 ounces, and the Sig P232 with 7 rounds weighs about 22 ounces. All are good choices. If weight is your primary concern then go with the M442. If power is your major concern then go with the Kahr or the S&W M640. If you like a lightweight, cool auto go with the P232.