Inthedetails
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Just thinking out loud.....
Say it was someone she knew, like a peer or something. And say that they wanted to talk to her before she left for NYC. Maybe it was someone she didn't so much hide from her parents but just didn't really feel like explaining. So she agreed to meet this person to "talk". So she just used her normal run time as her excuse to get out of the house to meet up with this person because she knew it wouldn't raise any flags as it was something she normally did.
As I mentioned earlier lots of local kids grow up knowing where these little off shoots into the woods are, because they are the same places to go "party in the woods" or take a girl to make out, or to go smoke weed. (Not saying Vanessa was doing any of those things). But it could be a place someone could have taken her to "talk".
Or perhaps they "talked" elsewhere like in the parking lot of the Mnt barn.
Either way it could explain why she might have willingly gotten into a car and perhaps been driven the 100 ft into the woods.
If they were talking there and things got heated maybe he straggled here and then left the body there and tried to cover his tracks.
It's a possibility that she met for a "talk," but I'm doubting it. She is a poised, polished, young professional without childhood ties to that particular town. She doesn't seem the type (yes, I'm making an assumption) who would sneak behind her mom's back at this stage in her life. I think when she left for her jog, she really wanted to get the exercise in that lovely setting before heading back to the city. She is an avid runner.
She also is attractive, petite....and alone. She was a random target just for those factors.
I think she was grabbed, or somehow lured, either into the car or onto that cart path. I really don't think the perp knew her personally, but I do think the perp was a local person who knows about the cart path. I don't think the perp targeted her personally, but simply because she was there.