A solid DAC/amp is never a bad idea, especially a USB one if you run from computer. It seems to me that you have some gear that you could flog off over at H-F to build up funds. Now, if you were to sell off the tommy, alo, and some of your lesser used cans you could probably fund one pretty good system rather than have a whole bunch of middling stuff.
I don't think the Pico is a bad decision by any means.