We all enter SP each night just before we start to dream, so I would say, we all are pretty good at it. It's more of the matter to stay aware during the process. This is the hard part, because you have to stay awake but then fall asleep just at the right time.
WILDing is not easy, because there is so many variables and all of them have to go right for you to achieve WILD. But you could be right, that first WILD may be the hardest, because you don't know the sensations and what to do. Subsequent ones may be easier, because you are already somewhat familiar with the process and what to expect. Although don't realy on that too much. Pretty much each time I WILD, the experience is somewhat different from previous ones.
Have you checked out Sageouse's WILD class in DV? It's a long read but really worth it. Happy dreams
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