[dayman]

Having the benefit of my own back yard pistol range I've practiced drawing and shooting from the hip a bit. Not a lot, but IME it's not as hard as you'd think. I'd have a hard time hitting a bulls eye, but at 10 yards it's very doable to keep all my shots within a standard silhouette.
I shoot at steel, so I don't like to get much closer than 10yds, but I assume a 12" group at 10yds would translate into a 6" group at 5yds which - while it isn't "good" - isn't terrible. And that's a shooter of moderate ability and maybe 100 rounds of practice.

I don't have one, but a crimson trace might be a good investment to get an idea of where you're aiming without having to shoot. I'm not sure that the laserlyte targets would work all that well for this as they tend to be kind of small, where as a laser sight would show you where you were pointing even if you're way off.
I haven't tried anything more difficult that shooting at static targets, and I imagine it would be trickier, but again it's probably just going to come down to practice..
I don't know how much training would help though. I started noodling around with it after I watched the hip shooting "top shot" episode where the basics were explained, and then it was just a case of lots of practice.

On a pragmatic note since hip shooting tends to involve bending your wrist a lot you probably want to use a revolver, or - if you're using an auto - make sure you're not bending your wrist enough that the slide could come back and bite you.
I've mostly used a ruger 22/45 and not had an issue, but using, say a 1911, might require a little more care.