Hmm... I have a VPI Classic 1. I've compared it to loaned CD/DAC's in my system.
Digital playback, while very precise and accurate, doesn't hit the emotional nerve like a good record on the Classic. IMO, setup with a cart and best phono state you can afford, may help you "see the light"
The Classic gives a good slice of what serious rigs offer, with some effort. The choice of cart, phonostage & settings all important.
Reissue LP's? Part of the problem.May as well stick with the CD or file.
My $0.02 of subjective opinion.