Seriously Searching said to start new threads when we start to hijack old ones, so here it is (not that I expect anybody to join in)
I don't think Cheryl was in her car, I think she was hiking along the road (which runs through/along the Apalachicola). Her purse was still in her car, which was found locked. Friends said she wouldn't have taken her purse (maybe it was one of those really big ones, so she just grabbed her wallet and left the purse) Anyway, it leads me to think she got out and started walking. So no, she wasn't out in the woods on a trail, but she was in an area with few houses and lots of forest.
Meanwhile, Hilton himself spent an awful lot of time alone on the trails - so it might more be having his victims wander into his territory, rather than him seeking them out...
He said with Meredeth he was looking for a female alone - and Cheryl fit that description for sure. Especially if she'd left her vehicle. Or even had gotten out of it to look at the tire and he happened along at that very instant - he offered to give her a lift, she locked her car and got in with him... With Cheryl, I think it was that an opportunity presented itself to him with a big bow on top - he probably wasn't looking for a victim, just happened on a situation too good to pass up.
I rather think Hilton has been doing this sort of thing for years, and there are a lot more missing women (and possibly older men) who were his victims. The whole story isn't told yet.