The way things have pretty much worked out is I do better if I can find someone(s) to spin tunes for me. Despite having a rather decent music collection, devices to play it scattered where I might be, and some time invested in software to spin it for me, I quite easily get into a rut when directly or indirectly I program for myself.
In some ways, the iPhone was a step backwards as a mobile device for me. However, after spending 9 days away, I arrived home to a discontinued, $10 fob which when attached to an iPhone or iPod, enables it to do A2DP (Bluetooth stereo audio).
Then, tonight, tiring of issues with my own cheap hack to stream audio on the iPhone, I found FStream... and I'm right back in business. I am still sort of sad I have to resort to importing radio stations, but hey, you do what you have to.