The ratio of funds needed to be spent on analog to match digital quality is significant (at least 2x or more). A $1K streaming DAC will easily outclass a $1K (TT, cartridge, phono combo). Disregard any talk about vinyl being better than digital, there are simply too many variables in the reproduction chain for that statement to merit any credibility. And then you get down to source material which is the most important factor:
Here are my best practices:
a) Generally listen to music in whatever format it was recorded (streaming/CD for digitally recorded albums and vinyl/tape for analog recordings).
b) Get your records from boutique audiophile labels / pressing plants (Analog Productions, Speakers Corner, Mofi, Pure Pleasure, Music Matters, Craft, OJC, ORG). In many instances, records from these labels match or exceed original pressings and you won’t have to spend your days praying and hoping that your soon to arrive expensive original pressing doesn’t sound like/look like worn out muddled dog shit.
c) Most vinyl records pressed today are mediocre. Learn about verifying analog chain of the record (if a record is cut from digital source, save your money and stream instead). Respect yourself and absolutely avoid European labels that make domain free pressings (Waxtime, DOL etc.)
d) My experience is that the best sounding records are the ones that were recorded and pressed in the 1980s right before CDs took over.
e) Discog reviews are your friend
f) Above all, mastering is key; try to familiarize yourself with the names of the best mastering engineers and studios. A well mastered dollar bin CD will run circles around a minty vinyl record with mediocre mastering.
Records are cool, but they are a lot of work to get right, and unless you are ready to obsess over a bunch of details, and patiently work through a raft of frustrations, you might be better off simply investing in your digital front end and enjoying the piece of mind that comes with that. I might sound a bit down on vinyl but it is still my preferred format (because when everything comes together it is a sublime experience).