Pros:
A short (but not overly short) and wooded (but not overly wooded) 9-holer that makes for a good warm-up or wind-down.
Shepherd has decent amenities, with concrete tees, fine baskets, and tee signs that include a verbal description of the hole shape. The terrain is also pretty good, with some short hills and plenty of well-carved woods to introduce challenge, but a couple of holes that feel a little more open. Other than the (3)-(4) and (4)-(5) transitions, navigation was pretty easy and intuitive.
The gameplay is a difficult recreational-level challenge. The woods will require accuracy, but the distance is short enough that it's still accessible to non-advanced players. The course opens with simple RHBH hyzers, but in the second half requires touchy tunnel shots and a right turn. The elevation definitely plays in to the mix, as a birdie drive will need to have decent angle control to stay parked and not make for an awkward straddle putt. (The elevation will also challenge you to see how comfortable you are at putting on non-flat ground.) I didn't really get in trouble here, but I think it would be fairly scramble-able.
Overall, Shepherd is a pleasant little course. It's got a little meat on the bones that make it not a total birdie fest, but there's definitely the possibility of trying to post a great round as well. As noted above, I think this would be a great course to warm up for or cool off from a day of disc golf--interesting, but not exhausting.
Cons:
The first and main con is definitely the maintenance here. Two baskets were missing when I played, which really sucks some joy out of a short course; they should ask East Brainerd for two of theirs. (UPDATE: Baskets have been replaced, which is a nice surprise!) I can't remember which ones, but at least two tee signs were gone or unreadable as well. Overgrowth looks like it could be an issue in the summer months if you ricocheted off a tree.
The baskets and tee sign situation also made for a little bit of tricky navigation in the (3)-(6) range. I found the basket to (4) before the tee. Then, it was a long, unmarked walk to (5), then a short backtrack to (6), which wouldn't have been an issue except that there was no sign to look for.
I have a couple of gripes with the design as well. (4) is the main offender, a dogleg so sharp that you'll need to play for a tree ricochet to be parked. The shape of the turn on (6) also seemed a little off to me, but not as bad.
There are also some safety things. I very nearly clunked the building, which is definitely in range of a reasonable shot on (7). On (8) you'll need to watch for walkers. In terms of the player's own safety, there are lots of tree roots and slippery pine straw hills that could easily roll an ankle.
It's also worth pointing out in the cons that this is a limited course. Nothing over 300' constricts the gameplay possibilities quite a bit. It's good for what it is, but it's not disc golf wonderland.
Other Thoughts:
Shepherd is one of those nine-hole courses that is just fine but doesn't have much uniqueness. It's like having three crystals of sugar placed on your tongue--faintly sweet, but not a memorable experience. Come and play some simple woods holes, then move along to an 18-hole course to actually have your game challenged.