How much do you need to spend to get digital to rival analog?

rbstehno nailed it. IME, for most audiophiles' analog or digital budgets (let's say $100 - $15,000) digital yields better quality sound. If this question were asked 8+ years ago, the $ range would be different. Between analog requiring a TT, a cartridge, a phono preamp an isolation platform not to mention brushes, record cleaners etc. there are simply many more components to purchase versus digital which as we know is a DAC and a  computer and now there are models integrating both into one. Once you get >~$15,000 things balance out. At the level I'm at (Aqua Formula xHD) + the convenience of unlimited music at your fingertips, spinning records has no appeal.

i have a 6 year old NAD D1050 and have not heard anything better lately under 2K.  you can pick them up for about $400. 

Very simple answer--Exogal for 7k. Absolutely wonderful sound that kills my former tube equipment with a far smaller footprint. Tubes are greatly overrated though lots of fun.

Depending on Budget. The Excellent Lampizator vacuum tube dac 
which received a 5 star rating in Enjoy the music .com 
is their latest entry level dac that is $2750: and by far the most natural sounding dac under $5k. If your budget can go higher their next step is around $6-7 k. The key is very good USB cable 
they distribute a small little known brand a Final a Touch Audio
Callisto usb cables by far the best cable I have heard and nothing under $1500 can beat it for its natural presentation especially after 
150 hr runin , it was so good I bought the cable ,their interconnects are just as good . Check out the Lampizator Amber3
dac .they even have a money back guarantee, and the USB  cable 
at around $800 a must if you want to hear proper digital thst sounds like good analog.