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Yes. They can sound better and when technology changes you can usually upgrade. Also multibit dacs or also called R2R or ladder dacs sound closer to vinyl then Delta/Sigma dacs Also the quality of the transport is important. You should know that if you ever play your own files that ladder dacs will not do DSD if that is important to you
Sound wise no, as in a cdp you have one clock which clocks both transport and dac together, which they say is far better. Where in separates there is a clock in each, and they are not locked together.
There was one or two very expensive transport/dac arrangements that had a separate clock wire between the two which clocked the transport to the dac clock, but these were very expensive units and rare. I think they were Wadia,Mark leveinson and Cambridge Audio Reference 1.
I am using the Schiit Bifrost Multibit DAC, but not with a transport, but for converting streaming USB music. For this configuration, I can say it really sounds 'cleaner' than my Rega Apollo or McCormack CD transport. I haven't gotten time to connect them to the Schiit, but if Georgelofi, says it wouldn't make a difference, then I would leave it at that.
I use a bifrost almost every day. It never fails me. Getting one with USB built in will make it much more flexible if you want to stream in the future. As you go up through the Schiit line-up you can easily notice sonic improvements which match your budget.
Another huge advantage of using an external DAC is that you can just upgrade that portion of your system.