IMO, I don't think you will get outdated with the Hugo 2 as your DAC since Hugo 2 has 4 filters AFAIK to cater to the sound you like while Yggdrasil is just a flat neutral sound and Gungnir Multibit is slightly warmer than Yggdrasil. The issue with Hugo 2 is the battery needing to service every few years in the long run. As for pairing to amps, it is best to stick to the analog stage output of the Hugo 2 rather than use another amp since Chord DACs sounds best without using an amp in my experience with Chord Mojo that I currently use for my travel setup.
Never heard of the Wadia 122, but if you can loan an Yggdrasil and compare with your friend's wadia, that should decide if you want to go the Schiit route or something else.