I had an fairly inexpensive audio setup when I decided to get rid of my 100 or so albums and inexpensive turntable. An article by Michael Fraemer made me decide to take another look at analogue. The first thing I did was buy a better cable from the turntable to the preamp. It helped a bit, but I'd be lying if I said it sounded better than CD. Then I bought a used Rega 3 for about $500. (This was mid-nineties.) Also a Sumiko Blue Point Special. I began to hear a bit of difference, especially in the Rega's speed as a result of its glass platter.
Fast forward through buying about a thousand albums and upgrading eventually to a VPI Prime Signature and Audio Research PH-7 with an EMT HD 006 cartridge, about $2,500 worth of gear. Now the main difference I hear with records is air. Even digital through my streamer at 192 resolution, which is damned good, lacks the air and warmth of a good analogue setup.
My main point is whether you feel committed to investing in analogue even though it might take a long while to upgrade your system, and even when you have upgraded, to be able to hear the difference. I guess my suggestion would be to visit an audio store or a friend who could demo a good streaming system versus a decent analogue rig. See what your ears tell you. Can you hear enough difference to invest time and money?