The thing about ancient Chinese philosophy is, it's ancient. As relevant as the core teachings might still be, the metaphors and original context sometimes suffer from antiquity so severe that many modern-day folks (myself included) simply can't relate, and therefore miss the message. These days one typically isn't faced with dilemmas such as how to most elegantly butcher an ox for ceremonial offering, or what to do with a crop of comically oversized gourds.
And from a Western point of view, the other thing about ancient Chinese philosophy is, it's Chinese. That is to say, it's incredibly foreign. Many Westerners (myself included) sometimes struggle to understand even modern Chinese culture, simply because Western and Chinese cultures differ so greatly. The two take radically different approaches even to something as fundamental as language: non-tonal pronunciation versus tonal, a phonetic alphabet versus a complex logography, etc.