Typically, these days you can equal things by carefully choosing and investing about the same amount as your analog rig. For me my digital and analog sound simply stunning and the same... as I desired. You can see my systems under my userID.
For systems that are more budget oriented, sometimes you may need to spend a little more on digital... say maybe up to 20%. But this is changing rapidly.
So roughly: Turntable + Phonostage = Streamer + DAC.
You have to put the same effort you would into choosing a TT, cartridge and phonostage into the Streamer and DAC. My rough rule of thumb for a digital system is 30% speakers, 15% amp, 15% preamp, 15% DAC, and 15% streamer, 10% cables and interconnects. Really generally. Same for analog 15% TT and 15% phonostage.