IMO, it all depends on the recording and on the playback equipment. Since you are just getting started, I would start investing in equipment that would really give your system a boost in SQ. IMO, going from a Yamaha CD player to a rega isn't going to get you ahead. I would invest in a really good quality external dac then hook up a CD player, music server/streamer to it. As for vinyl, get your wallet out. You will need a good phono preamp (much better than using 1 inside a receiver/integrated amp), then a good tt/arm/and cartridge. You see all these reviews comparing vinyl to digital and the reviewer always prefer vinyl. But when you look at their analog equipment, they can have up to $250k in a tt/arm/cartridge/phono preamp, and they compare this setup to a $15k digital setup. It takes quite a bit of $$$$ to build a good analog playback system, much more than building a really good digital system. I propably have 3x more invested in my analog setup (retail prices) compared to my digital equipment and I have vinyl albums that blow away my digital albums and I have cds/dsd albums that sound much better than vinyl.
1 option when you go analog, you can setup a 2nd arm with a mono cartridge and get superior sound over its equivalent stereo album, if the album was produced originally as mono, not converted, for example, miles Davis kind of blue and the Beatles mono collection.