I'll bet a dollar it's more about bandwidth than concern with violating any laws, as the laws do not specify HD or SD.
As for WWOR, it's on a spotbeam to conserve bandwidth. And, Dish allows those who sub to it as a Superstation outside of the DMA to receive it in HD. I'm sure they would do the same if it were CONUS. But, it seems obviously, they don't want to devote those limited CONUS resources to Supers. Many folks would love it if they did. But, I guess they don't feel it would be enough to justify the cost.
I doubt very much they care about making waves with the networks and affiliates, as that never stopped them before. Nor, fear getting in dutch with the gov't, as no laws seem to forbid it.
That is an excellent point. Why waste bandwidth putting up multiple feeds of stations that are known primarily for CW and MYNetwork content.?