My guess is that the OMN concept is something Steven Lowy felt passionate about, and genuinely believed could be a success, and the rest of the family backed the project to support him. I don't think Steven Lowy is in it for status or money, since as you've point out he's had plenty of success with both already.
Agreed. It seems to me that there's not much upside for OMN to stay listed, but plenty of downsides, e.g. management having to waste time with reporting requirements, extra costs of maintaining an ASX listing. I can't even see them getting the main benefit of being listed, which is ready access to growth capital, given their low market cap relative to funding requirements. I don't see them raising $150m-$200m when their market cap is $105m and rapidly declining.
Does OMN even have that much of an Australian connection anymore after the demerger? The company now seems to be almost entirely American - American partners, American / UK target market, american management and executives. Not sure why it should have an Australian listing.
Adding it all up, it just seems to be only logical that OMN be taken private at some point. Maybe Steven Lowy could form a consortium with some US venture capital firm and buy OMN holders out. Would seem to be a sensible course of action for the Lowy's to take, imo.