Loveys take awhile for the novelty to wear off. Usually they are given at a younger age, but you could try again. Sleep with it a few nights so it smells like you. Use it when you cuddle him and/or feed him if you still nurse or do any bottles. Give it that snuggly, mommy, sleepy association. Then go ahead and try again. My DS just recently started asking for his this past week. It is an elephant head attached to a blankey square. When I take him to his room he says "Phant?" and looks for it. I give it to him, he let's me rock him while singing rockabye baby and then I lay him down and he rolls over, gets comfy and goes to sleep.
As far as methods go, he'll probably resist WI/WO a lot stronger than he would a GW, though he WILL protest both. He's not going to like the change, no matter what it is. The WI/WO will probably work faster overall, b/c once he learns he has to fall asleep alone, that's it. When he accepts the change, he'll find a way to soothe himself. With GW, although gentler, he will accept the change, then accept the change from lying on you to touching your hand for example, then accept the change from touching to seeing you, then accept the change from seeing you to hearing you, then...and so on and so on. Then the LAST step is still to accept the final change of going to sleep alone and finding a way to self soothe. So it takes many more steps before he gets to the stage of learning how to get himself to sleep. Generally, speaking anyway.
So for deciding on a method you have to ask what you think would be best for both HIM and you. I always liked faster methods but that was b/c I hated dragging out the ordeal and I was usually always working full time. Plus my kids tended to not fall asleep with me present at this age as it seemed to rile them up that they could SEE me but I wouldn't pick them up. They are both a bit spirited though.
