I don't know if this helps, but Live is not like other sequencer programs. It takes a little while to pick it up, but it becomes second nature. And, like many things, it is its own reward. It's pretty close in some regards--more like ProTools than Logic, say.
There seems to be a sort of bug that makes some files very small when you drag them into the arranger. Try zooming in extra close to see if there is a very short version of the file. You can then drag it out to its full length.
You can also place files directly into the arranger using the file browser. Have you tried this? It should give you a better handle on how to drag clips around and place them.
I use Live every day pretty much and I've had no problems coming to grips with it. Any good tool has some kind of learning curve, even a hammer. you just have to put in a little exploration time and you'll totally get it.
And the manual goes over this stuff in the chapter about the interface and in the one about the arranger.