Thanks for the input. Signage is sort of a weak spot for us. The trails get built, then we start riding, then we need to do maintenance, and we still want to ride some, and that last step to completing the trails keeps getting pushed down the list. Not a great excuse, but it's all we've got. The bottom of Pleasant View is definitely not intuitive. Sometimes it takes a fresh set of eyes to remind the folks who spend a lot of time there of that. We'll move signage back up the priority list.
The jump line is unlikely to get signed better. It's slated to be rebuilt, in part because it isn't clear and there are crossings. Believe it or not, it used to be worse. It actually is intuitive if you have some experience, but I can see how it doesn't look that way. Probably the best way to get a better feel is to come out on one of the remaining Capital Brewery Tuesday/Thursday rides, or otherwise hook up with someone experienced. For what it's worth, the sequence is; start at the picnic table area, 90 degree right berm, 180 degree left berm, go right at the fork before entering the woods into a 180 degree right berm, over the step-up, cross the exit trail, 90 degree left berm, then the jumps.
By skills area, I assume you mean the elevated sections down in the bowl. They are something fun to stumble upon; they could be better signed/promoted, but there is, as you say, some fun in discovering things.
That two track is not official trail. Some folks who are uncomfortable with the steep side-hill before the first bridge like to go that way; it just follows the power lines and you hook up with the real trail at the first short prairie.