Mike,
I have shot the LCP and was pretty impressed with it. Not a bad CCW piece at all....especially for the price. The trigger is fair at best and the pistol my friend has did have a few FTE's at first. May have been the ammo or just the fact that the pistol was new.
What kind of holster and belt are you using as this can make a world of difference? You are spot on in your thinking that if it is uncomfortable, you probably won't carry.
While the 380 is certainly better than nothing, I would feel much better with a 9mm or bigger. The subcompact XD would be an excellent choice as you are already familiar with that platform. The sub compact Glocks, Sig 250, and S&W M&P would be excellent choices as well.