RoS, you've addressed all sorts of reasons related to your perception of how important the whole Masking issue is to believability. Oddly, most of my players wouldn't bat an eyelid one way or the other. So I'd call it a very small corner of the game and therefore not that significant either way.
But having said that, we aren't aware of every property of matter nor of alternate spaces. I'm not saying it is likely that something in our 3-space will exhibit a matter-based (ie radius based) property that is not related to density on some alternate space (Jump Space), but really there isn't any basis that I can think of to say that it isn't possible.
And you've missed, IMO, the most important part of the game aspect - Masking has some interesting consequences for players in the game. Gravity based shadowing could work too, but I have run into systems where it would *really* bugger up commerce. You'd have to rewrite a few trade lanes as a consequence and while we're at it, why don't we talk about revamping all the UWPs to see populations distributed where it makes some sense for trade or for planetary habitability? I think you start tugging at one thread, many things unravel. But Masking, as an idea for a role-playing impediment, is fine. It serves that purpose admirably. It has shortcomings, but I suspect more for those who (as Larsen puts it) 'play with Traveller' than for those who 'play Traveller'. Heck, those in the latter camp don't even mind the mis-spelling of vaccuum.
To summarize:
1) There is lots of existing canon
2) There is no pressing reason to change it (you could argue there is a need to clarify it)
3) There is a role-playing function that it serves
4) There could be some property of matter that is not related to density that applies here. I'm not sure I have any idea what, but usually when people say what can and can't happen, in the long run, they're proven wrong or partially wrong. In this case, I'm willing to buy 'Jump Space' so I'm more than willing to buy 'Jump Masking'. The whole ecliptic issue is a red herring because it could easily be that all of those objects arrayed at varying Z values in our 3-space map to some sort of flat plane in J-space and thus the ecliptics are utterly irrelevant. We don't know... and thus... it all boils down to speculation... and I think it is fait accomplit.
Fill yer boots, evangelize for the change, but I think you should be prepared to be disappointed.