Lots of questions, I'll reply to everything I can
I really liked the Senns with the Hugo 2. I thought it did a great job with it.
This is the only Chord product I've owned so can't compare to Mojo.
I never heard the Topping combo (although, the A90 is possibly a future purchase). I have the Hugo 2 and now the RME that I got recently. I've only done a bit of comparisons, super crazy busy these days, so no time for critical listening, but so far I either hear very little difference (more power with the RME than the Hugo 2), or none. I would like to do some blind tests, but that requires my partner to play along which I'm not sure will happen lol.
So,
for me, the Hugo is going. It costs more, so I will be "making money" by keeping the RME and selling the Hugo.
If I needed a portable device, I may have kept the Hugo but for now that is not the case.
I currently have the Abyss Diana Phi. I bought the Abyss Diana V2 and liked it. When compared to the Focal Clear and the HD800 that I had, it did everything those did, but better (except for that insane soundstage the HD800/S have).
I sold the Senns and the Focals because I don't collect things and don't want to keep things I don't use.
Before that I had a few others, but the HD800/S is maybe my favourite headphone. I bought and sold it 3 times and had the S as well for a little while there.
After getting the Diana V2 I then had an opportunity to get the Diana Phi so I did. I compared the V2 and the Phi and decided to keep the Phi. The V2 is now gone.
I have a Mr. Speakers Ether 1.1 here as well I just got (for my partner) but I haven't had a chance to listen to those yet
(I've been enjoying the Phi too much).
If you ask me if I think it's a good buy, I'd probably say no. I think that the Senns are my "best value" as much as that can be said with regards to things this expensive. Diminishing returns and such play much more above these prices and the differences are usually not the "night and day" reviewers and companies would like you to believe. For me, at this point, it was the right decision.
As I mentioned, I don't have the A90, but from reading both the A90 and the D90 are also pre-amps (one in the digital domain and one in the analog domain), so you should be able to connect to speakers. You might need an XLR->RCA adapter with the D90, but the A90 has RCA connections so you should be able to connect these with that.
That said, some people mentioned some ground loop noise when using RCA connection, so YMMV.
I believe that if you look at the picture of the front of the A90 you could see the leftmost switch is an output selector and you can switch between headphones and pre (pre-amp - your speakers in this case) meaning you can connect both at the same time and choose which one is going to output music (but I believe you cannot have both playing at the same time, again I'm only reading here and don't have experience with the Topping combo).
I hope I didn't miss anything. Let me know if you have more questions.