Well duh. Of course it doesn't. The best 16 bit home kit isn't as good as the best vinyl transcription. Lots of vinyl playback sucks as well but when comparing formats you need to compare the best available or you're comparing kit instead. A technics with a MM cartridge is not a good foundation for format evaluation. The best analog costs A LOT but so does the best digital. Thats where you compare formats, where the playback limitaions aren't as severe. It's difficult to get TTs right but extremely rewarding as well.
I can easily hear the difference/improvement between a proper vinyl transcription of 16 and 24 bit dubs on top kit. That would indicate that vinyl has more to offer than 16 bit can transcribe. TTs are tough because so much of the playback chain is often colored but that's kit and not format. I find many opinions senscere but inexperienced when it comes to much of this.
I'm fairly sure its not the format itself, rather its the sucky implementations that are offered of digital - replete with noise modulation. If you got yourself a top grade TDA1541A DAC with all the enhancements and decent output filtering you might begin to see (or rather, hear) 16bit rather differently I suspect. Just my conjecture