I'll begin with those questions which are shortly answered:
2) besides the Lupine SL-F it is by far the most effective road light i ever owned and i never want to go back to use anything with less output again (although the Ixon Space on the highest setting does a very good job)
4) it is a very solid designed and made light, no flaws on it. Someone with brains sat down there and designed that lamp well from the ground up. Tastes differ, so some people might find the design "ugly".
5) i bought the Outbound Road after buying a Lupine SL-F (which has a dipped beam and an additional high beam). I bought it out of curiosity and because i wanted to support a project which designes specific and high powered road lights. Imho there are not enough. I intend to use both lights in future in parallel to always have a backup light, with the OL Road as main low beam lamp, since it has a warmer beam color tint.
Now those answers that are bit longer:
3) Since in germany non cut-off lights are not allowed on roads, (and i try to be good citizen) i never used one, always had a StVZO cutoff lamps (before i used a ixon iq premium). So not really hard to get used to for me. The issue and limitations of cut-off lights was for a long time that the light output was just too low for higher speeds, but this issue is finally resolved since the advent of lights like the Ixon Space, the Lupine SL/SL-F, the Supernova M99 lights or the OL Road. (Actually it was resolved by the advent of the B&M Big Bang (HID/Gas discharge lamp, but that was even for my liking too expensive)
1) Illumination: well enough to cycle securely with speed up to 22 mph. That is the most i can achieve for a longer time on a flat road, and the same speed i reach by day.
There is imho one little weak point in the light distribution of the OL Road: If the cut-off is adjusted in the "good citizen" way, i.e. just not blinding others, the area in front of the bike is lit/lighted up a bit too bright for my likes. On the highest setting on bright gravel this is a distracting, on darker tarmac this is less of an issue. See
this post of mine (but keep in mind that camera settings used there were not adjusted to give a most realistic beam shot, it was more chosen to show that "too bright" spot. In case of the the first two images there, the gravel path was for the eye illuminated at least up to the reflective road sign, which was ~160 ft away)
Cut-off limitations:
There are situations on the road where a high beam is nice, but not necessarily needed. Then there are situations where a high beam is very useful or necessary (i.e., when you have the risk of crossing deers, or you speed down a hill above 30 mph). I enjoy the high beam of my SL-F, and i use it if there is no oncoming traffic, just as i use the high beam on my car. But since you have a few conical lamps and a helmet mounted light, you could use these lights adjusted to max throw as additional high beam lights in those situations.
Also, the OL Road can easily be adjusted while driving to a "high beam" lamp (when using the silicon holder, which is rock solid if not moved by hand, see here in this video youtube.com/watch?v=0WNN1Wvq2_U )
I personally think a cut-off light would complement your light setup very well. If you are a bit reluctant, get a Lumintop B01 on banggood or aliexpress first, <40 USD. It is not totally glare free, but mostly, and if you like this type of beam, think about the OL Road or the Ixon Space (both lamps make better beams than the Lumintop, what i have seen from pictures) The Lumintop B01 can then be used as flashlight for all purposes...
And there is another weak point: on my OL Road version, i have an automatic step-down (by two brightness steps) from the highest light setting once the runtime drops down to 50%. That cannot be overriden, you can only go up one brightness step again. I don't know whether that has been changed so far, but since OL offers a 30 day money back guarantee, you could just try the light and see whether it fits your needs. Probably one could solve this by using a li-ion battery with 3 cells in series (11V) or by just using a bigger battery pack to have more usable runtime on high. The lamphead is also available without battery for 140 USD.