In my opinion you should also be mindful of your vinyl source for your comparison to your digital because you don’t want to just compare a digital vinyl record (reissue/new) to your lossless files for this test.
Aim for as close to original pressing as possible, of course, and I think some favorite Blue Note recording from the late 50s would reveal the most dramatic difference to your digital files of the same recording... if any.
Of course I am biased since my vinyl set up has developed to get the most out of vintage jazz that I found less than engaging from digital source but now find intoxicating on vinyl.
Aim for as close to original pressing as possible, of course, and I think some favorite Blue Note recording from the late 50s would reveal the most dramatic difference to your digital files of the same recording... if any.
Of course I am biased since my vinyl set up has developed to get the most out of vintage jazz that I found less than engaging from digital source but now find intoxicating on vinyl.