Which Streamer/Dac

Sounds like you are on the right path. Sim makes very well built quality components. While I would purchase a separate DAC and streamer. 
 

I would not worry about a ripper. You can always do it on a PC… although these days there is less and less reason to do it. A great streamer and DAC will negate the need for any stored files.

Getting the best sound quality / quality components will provide the best long termed solution. So, I would get the Sim. I have owned several SIM Moon products.

What is the rest of your equipment? This is necessary and it would be really helpful to see your system. There is a place under your ID to create your virtual system. 
 

My rule of thumb is that the streamer and the DAC should be at the same investment level as your preamp and amp. If you are building a system over time then separates make much more sense than combo units.