Inexpensive Streamer for Office System

Wiim has a good range of inexpensive streamers

Maybe BlueSound? Several models and all within your price range.

I evolved my office headphone system somewhat like you did. 

Bluesound makes some very good little streamers. I have a Node that I use for breaking stuff in. 

Just a note on headphone systems... it's all about the head amp. You can see where I have ended up after many years. My systems are under virtual systems. But a headphone system can be very very close and satisfying as a main system. But the same commitment, effort and careful choice in components gets you there. 

So, a word of warning... it can be like the pursuit of an high end audio system if you have that personality. 

Have the Bluesound streamers improved with time?  I remember listening to their gear when it first came out and finding it a bit "hifi" in nature.  But that was many years ago.

And thanks for the words of warning.....I can already see where this process will ultimately end up; though it will evolve more slowly than my main system.

get an old auralic aries mini or a bluesound node with lps mod -- easy peasy, dead reliable, sounds good