Gavra, the Gemara at the end of Kiddushin sys that there is no profession without poverty or wealth so someone should not choose a lucrative profession but a clean and easy profession. Some interpret this to mean a profession with a minimum of moral dilemmas whereas others interpret to mean a profession that does not require a person to work, as the saying goes in Hebrew “metzet hachama ad tzet haneshama” (thus many frum Jews work in civil service postitons). However, you are right in saying that one has to normal hishtadlut. If he does not succeed he should at least learn to see where it takes him.
As for the time of Mashiach, Rambam says that at the end of Hilchot Melachim. However, IMHO it means that we will be a nation of think-tanks that will supply legal opinions to the Bnei Noach for money (thus they will support us without feeling that they are giving charity0.