It's certainly true that some trail designs shed water, minimize erosion, and maximize sustainability. Rolling grade reversals on bench cuts into mineral soil on moderate hillsides is one such design.
However, there are many considerations that a trail designer takes into account when walking the land and visualizing a trail. Moderate hillsides aren't always available where you want them, the soil isn't always optimal, and you have to work with what you have to craft the mountain biking 'experience' you're looking for. Interesting experiences come from breaking the rules - fast downhills, steep climbs, tricky switchbacks - those are the features we remember. Any good designer considers water flow in their work, but to get from one place to another, sometimes you're faced creating a segment of trail on flat land that doesn't drain well. The soil's going to compact, and you'll have mud hole and pizza cutter issues like this. Those are tradeoffs that you make in a trail design, recognizing that you are losing something to gain something more valuable - more trail, a better experience. Armoring and repair of these areas is routine maintenance that you grudgingly accept and plan for, in the same way that you might plan on having to rebuild a bridge every 15 years, fix the lip on a dirt jump, or redefine a berm into a favorite corner. That a trail requires maintenance doesn't mean its poorly designed.
I've had very little to do with the design of the Lakeshore Park trails. It's a trail system that requires a lot of maintenance each year, even more now that its gotten so popular. Soft loam over non-draining clay, intersected by wetlands, less than 35 feet of elevation over the water level of Walled Lake - of course there are water and rut issues. It's flat - there's just no place for the water to drain in some areas. Despite these maintenance issues, I think it's actually a very well designed trail that makes the most of the land and providing a pretty interesting, varied experience out of a non-optimal site. Fortunately, it's well loved by enough people that the maintenance never seems overwhelming.
Maybury could use some work. We had some focused trail work last year, trimming and filling in some muddy areas, and the DNR has armored some trouble spots. Our last large trail day was a couple years ago where we fixed some significant problems:
Perhaps we can do more this year.