Regarding point 2, I wonder how much of a benefit Itanium would see from JIT-compiled languages, because the JIT could then dynamically arrange instructions to maximize ILP.
While I certainly think this would make for interesting research, I think the runtime-complexity of VLIW algorithms (such as Monica Lam's "Software Pipelining") would definitely interfere with the upper-bounds for compilation time of JIT compilers.
(But, then again you could always use a background optimization thread...)