I have a CCW permit and the majority of the time I carry a S&W 642 .38. However, when attire allows, I carry my XD .45 compact. At least in my neck of the woods, KY, the malicious intent argument over caliber and bullet design is a non factor. Around here, people figure that in the situation where a gun would be used to save your life, it doesn't matter if you're shooting a .22 or a howitzer. Your choice of handgun caliber should not have to reflect the amount of "dead" your attacker wants to make you. As far as bullet design goes, cops use hollow points and they are never accused of maliciious intent because of it, so why not private citizens. IMHO, only hollow points should be used in order to prevent accidental injuries due to over penetration. In response to your last question, in Kentucky, the only illegal ammunition is armor piercing, so even if the police wasted their time checking your choice of ammo, they would have no beef with hollow points whether they be .22 or .50, handgun or rifle.
Swoop