William Johnstone points out (1 & 2 Chronicles, 1.15–16) that the Chronicler’s chronology “is related to the jubilee (Lev. 25:8–55): in the fiftieth year ‘you shall return, every one of you, to your property and every one of you to your family’ (Lev. 25:10). For C, the exilic generation is the fiftieth generation since Adam (10 generations from Adam to Noah; 10 generations from Shem to Abraham; 30 from Abraham to Josiah makes, by the deduction of one for the repetition of Abraham, the generation after Josiah—the exilic generation—the fiftieth generation.”
Thus, “the exilic generation—to which he himself and all his readers after him belong—is . . . the one to whom the proclamation of eschatological jubilee is made.” Johnstone points to the parallels between Cyrus’s “let him go up” and the proclamation of Jubilee in Leviticus 25:9.
That’s intriguing, but it works only if you conflate the exilic generation with the generation that returns from exile. Judah is sent into exile to give the land the rest that it has not had during the period of kings; the land is going to have its Sabbaths (2 Chronicles 36:21). That means the exile is super-Sabbath of the Jubilee. The next generation is the generation that returns to its ancestral property. In Chronicles, the Sabbath rest for the land and the Sabbatical return are sequential rather than simultaneous. In Leviticus, they occur together.
There are at least two ways to deal with this. First, the Chronicler might consider the entire period from Nebuchadnezzar to Cyrus as a “generation” for the purposes of his chronology. During that period, the land had rest and (eventually) Israel returned home. A more paradoxical way to harmonize the Chronicler’s chronology with Jubilee is to suggest that the expulsion from the land is itself a “return.” It is in a literal sense, since Israel came from Ur when Abram did. That would imply that what Cyrus proclaims is less a Jubilee “return” than a new situation for Israel, not a “going back” but a “going up.”