It has been repeatedly reported USB should be avoided to simultaneously stream onto a DAC and to connect a HDD, because of the serial nature of USB. It will work, but optimum performance is to be attained buy avoid USB for both.
So assuming your external HDD is USB, consider another HDD as an upgrade path.
+1 on the suggestion to use the ripping guide found at Computeraudiophile. I used it to set up dBpoweramp the first time and works great.
Look around for comments regarding JPlay. Many say it's the best software in terms of sound quality. It runs on top of JRiver and improves the sound, while using the excellent interface JRiver provides. However, lately JRiver has taken issue with this and a danger/malitious software banner appears when JRiver detects JPlay is also being used.
So assuming your external HDD is USB, consider another HDD as an upgrade path.
+1 on the suggestion to use the ripping guide found at Computeraudiophile. I used it to set up dBpoweramp the first time and works great.
Look around for comments regarding JPlay. Many say it's the best software in terms of sound quality. It runs on top of JRiver and improves the sound, while using the excellent interface JRiver provides. However, lately JRiver has taken issue with this and a danger/malitious software banner appears when JRiver detects JPlay is also being used.