That is a weird question... You're saying it like the Hugo deserves a better amp, in which case I think you don't give the vio enough credit. What amp does your friend think would be worthy of being plugged into the almighty Hugo?
Anyway my 2c -
Firstly - don't worry about what other people think is a 'waste' or not - go by what you hear and like. In some people's system the dac is the most expensive part.
If it was me in your position I would compare the hugo+v281 which you already tried vs v850 (or v800) + v281 and see if you think there's much difference between the dacs. If not, sell the hugo and put the money toward the new system to make it more affordable. But also consider the difference between those and the hugo by itself - if you're happy with the hugo, it costs you $0 in system upgrades and you have the advantage of portability - the moment you buy one piece of desktop gear you're anchored to the desk - is the fact that you have to sit in one spot from now on a concern? If the difference between the hugo and vio gear isn't massive to you, and you use the hugo anywhere else besides your computer desk, it seems like you'd be crazy to get rid of it...
I would have thought that since the hugo is a pretty analytical piece of gear and so is the hd800, the sound might be a bit sterile when combined so maybe replacing the hugo with the v281 will bring a bit more musicality to the system?
A little while ago I was trying the v850 vs yggy into the v281 and since the v850 has a volume control, you can match the volume levels of the two dacs by using the XLR out of the v850 with the volume dialled back a bit and the rca's out of the hugo and instantly switch between XLR and RCA on the v281. You can loop the spdif in and out of the v850 or whatever so that the one source can output digital to both dacs at the same time and both dacs can output into the v281 at the same volume at the same time to make the comparison easier - you can just switch back and forward between xlr and rca and instantly compare the 2 dacs at the same volume at the same part of the song. If you don't think you'd miss the hugo dac too much you can comfortably sell it then knowing that you're comfortable with the comparison...