2. For LIL markets, the answer is "yes"; to get digital distants, you MUST get LIL, unless you're a pre-SHVERA subscriber to digital distants. I'm not 100% sure if that's true for grandfathered analog distants customers, however.
3. As long as D* or E* can find a station that carries ANY network in HD, then if they carry it at full bandwidth and meet the time-zone restrictions, they can launch it to eligible customers. That's the beauty of the "statutory license" (or "compulsory license" as they call it in the music business)