Excellent explanation as usual. my friend. Yes, there is much to be pondered...With nothing but respect, this actually presents a classic example of the tendency in Jewish tradition to conflate two different ideas: part "z'man ha-mashiach" or the world after the mashiach comes, and part "olam ha-ba," the world to come, which is more of a celestial afterlife type of deal....
In addition, one must wonder what happens to the soul while we wait for either of these two events occur... where are the souls of our loved ones right now...
I too am in doubt if the resurrection happens during the Messianic era, actually. I think the people of that era will be physically no different than us, but what they do with the world is what will be different. There still will be war, only it will be war on disease and suffering.I have said before on many an occasion elsewhere that it would behoove us to sort this out. Because while I have no problem believing in mashiach, or in a messianic world, I don't believe that such a world will result in its inhabitants having eternal life, or even necessarily freedom from trials and tribulations...
I have often thought that the resurrection happens after the Messianic era, indeed long after even the earth exists, even after the universe exists. There is a Midrash that this universe is the sixth one that HaShem created, and he destroyed the others as they were unsatisfactory. We are beings designed to be physical, unlike the angels. I have no idea what we would do for all eternity, as spirits. Strum harps? Not what I would choose. What I think is that there will be a new universe, after this one is done, and the resurrection of the dead will be into that new universe. What is impossible to HaShem?