You'll actually have a very difficult time finding a modern lossy encoder at sane settings that will produce anything worse than what's achievable with a vinyl record. Because modern oversampling D/A converters are also very good, very abundant and very inexpensive, you'll have a similarly difficult time finding a digital playback system that's more poorly-equipped at the task than a purely-analog playback system.

From a purely technical perspective I'll pick a typical lossy file over vinyl every single time.