For me, it's been part of a longer trajectory towards the appreciation of "the mess" in all of its dirty glory. I've always been an "algorithm" person: find the underlying pattern that gives beauty and stability (the two being synonyms, of course!) to the apparently chaotic world around us. Increasingly though, I've come to find that discrete difference has its own beauty and instability (the two being synonyms, or so I keep telling myself) that I had been blocked from appreciating.

Less philosophically and more pragmatically: during a time of reflection I was thinking about how my demand for precision was limiting my social interaction. I hadn't been as big a douche as some people I knew, but I could see more of myself in those people than I liked to admit, and realized I needed to change. But I can never change if I'm right, of course!

So I began to talk with people I knew were smart but didn't have the same penchant for demanding precision. On their testimony, I came to believe that there must be something good in ambiguity, though I couldn't comprehend what. I began to practice 'not objecting' when someone would use language or ideas ambiguously. This was immensely frustrating, but I vowed to let it be and try and find the value. Enough times of getting a glimmer of insight led me to finally admit that there was something worthwhile in ambiguity, and so I changed my mind.

There's an aesthetic component, but mainly it gives flexibility & speed. Think lossy encoding, or maybe dynamic typing.

It's important to note that advantages are not necessary. It wasn't designed. It could just be that it's so widespread that it's impossible to change.