Thanks, awakephd. I agree with most of your comments, and have come to the same conclusion as you for myself -- bought an SDS814X HD earlier this year, as soon as its upgradability had been confirmed here.
Some of your assessments do come across as a bit too clearly pro-Siglent for my taste. Since I also had the opportunity to use the Rigol UI (although on the DHO1074), let me add a few comments of my own:
- External power supply: I am not a fan either, but don't see why it would be a problem. You can always attach the power brick to the back of the scope using Velcro (or a 3D-printed bracket if that's your thing). The complete unit of Rigol scope + power supply won't be larger than the Siglent scope.
- Portability: I don't care about powering the scope from a power bank -- the limited operating time would make me nervous. But "portability" can also mean taking the scope somewhere else where mains power and a desk are available. I take my scope on train trips somewhat regularly and would appreciate if it took less room in my suitcase.
- Web interface: Like you, I don't miss the HDMI output but use the web interface regularly. I wish it had a higher frame rate on the Siglent, which Rigol somehow is able to achieve. (Yes, I know -- I am not a "good" Siglent user since I like to look at wiggly lines on the screen rather than setting up proper measurements. Seriously though, interactive use of the scope is important to me. It's totally fine when using the touch screen/knobs/mouse directly, but could be smoother via the web interface.)
- User interface: I have certainly struggled with nested side menus on the Siglent (e.g. to set up protocol decoders and triggering) and found that the Rigol UI made the task much easier. On the large screen of the DHO1000 the UI was great -- I wish Rigol did a better job optimizing it for the smaller screen of the DHO800, like with mrisco's tweaked UI. I also liked the dual flex knobs on the Rigol front panel.
Long story short: The Siglent, in my view, is the more "serious" scope -- sampling rate, FFT capabilities, Bode plot capability... But I can see that the Rigol's form factor, VESA mountability, HDMI output, and the "friendlier" UI may tip the scale in favor of the Rigol for some users. The current steep discounts on the DHO800 may also influence the decision.
The DHO900 is a different matter though. Paying extra for its logic analyser capabilities and finding yourself with a scope that has 600 MSa/s left for four analog channels just sucks...
Excellent points, and I especially appreciate the insight and correction you bring from having far more experience, including with a Rigol scope.
A bit of further comment / clarification on a couple of points:
With regard to the power supply ... as I said above, for most people it probably is a wash. I still say,
for my situation, I am very glad not to be dealing with an external supply. Attaching it to the back might help a little, but still would mean having to deal with two cords instead of one. And it feels like a kludge to have to come up with something that doesn't get knocked loose, while not blocking the ventilation ... but again, I am speaking for my situation; I can certainly understand that it might work out differently for someone else.
With regard to web interface frame rate and UI - I hope I did not sound like I was making any claims about how the Siglent UI compares to the Rigol. I only meant to say that, for me as a newbie, not knowing what I might be missing - having no comparison other than the little bit of experience using the Keysight - I haven't felt disadvantaged by the Siglent UI. And I didn't even know its web interface frame rate was slower, so haven't missed what I didn't know to miss! If I ever have a chance to try out the Rigol, I might well feel very different on both points.

I very much appreciate the balance you have added to what I offered above, and the far greater experience you bring to the question. Things like what else portability can mean - I never thought of needing to travel with the scope (can't imagine that I ever would), but now that you mention it, it makes perfect sense: when it comes to packing, smaller and lighter = better!
Bottom line: You and so many others have offered so much insight to me along the way, and have continued to do so, and I very much appreciate it!