Isaac,
So I've got my maps out here. Unfortunately they're not doing much to help me with remembering the exacts routes I've taken. So, I can't do much for specific trail recommendations but I've still got some info. Anyway, the Joyce Kilmer Memorial is what I was referring to as the 'drive-up' day-use type area. There are a lot of cool trails through the old growth there but it's not really a wilderness area – lots of day-trippers. I'd definitely make a stop there though – it's worth seeing. Based on my map, it looks like you CAN connect up with a couple different trails that go into the wilderness area. I would recommend checking all this out on a map for yourself though (I'll post a photo of the map I have below). It looks like both the 'Naked Ground Trail' and 'Jenkins Meadow Trail' could be accessed from that area.
I've hiked both of those trails and they were cool. Jenkins Meadow meets up with the 'Haoe Lead' and takes you to the Haoe Peak (5249). Citico Creek Area is on the same map and does border Joyce Kilmer-Slickrock on the west. You can easily access the Citico Creek side via trails that begin in JK-Slick and vice-versa.
Stratton Bald is cool area that's worth checking out in the southwestern 'corner' of JK-Slick. There really are a lot of opportunities for different loops and plenty of different places to park. Coming from Asheville, we usually parked along the eastern edge of JK-Slick. Either at the trailhead near Rattler Ford Campground (close to the memorial forest area) or at the Big Fat Gap trailhead (quite a bit further northwest). Hopefully these names/places will make more sense when you're looking at a map.
Regarding your concerns about getting lost/route-finding I guess I would just say pay attention. Like I said, I didn't think it was bad but it's very likely that you will have to stop and figure things out a couple of times. If that's not your style you might wanna check out GSMNP. In my opinion though, the area is so nice and the solitude you'll get make it worth it.
Also, I found my map for the Wilson Creek Area. Maybe you've check it out already but I really enjoyed a trip I took there. Really really nice waterfalls. It's in the Pisgah near Mortimer, NC. Good trails and nice opportunities for loops in there as well. I believe both of these maps (along with the Snowbird Backcountry Area, the map for which I can't find) were all purchased at the Forest Service Office in Asheville. However, I lived there before the REI opened up in town so that would probably also be a good place to check for maps. Here are the maps I've used for JK-Slick/Citico and Wilson Creek:
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That's what I've got for now Sir. Let me know if there's any more info. you're looking for. Later.