All the ideas are good from fellow audiophiles with regard to getting a streamer or ripper like the Sony, r2r ladder DAC and even new speakers. For sure, you could improve your sound tremendously with better speakers. Vandersteen, Magnepan and even the newer Paradigm are exceptional.
The only thing suggested that I would have reservations about is saying CD players are out dated or the combo of a new transport and DAC cannnot give you really good sound. I mean many people bet the farm that turntables were outdated and vinyl would never come back. Well many people are eating
words, and a much larger group are convinced analog is better than digital. I think CD players will stick around and DACs are getting better. I tend to stream now, and really like MQA but I think record albums still sound fantastic as do some CD players with a good DAC.
Some really like the Bluesound Vault 2, and it does everything you want. I have the Node 2 and it is the best digital sound I have had... for awhile.