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My first question is: did you manually move MiLB team's players onto new teams? MiLB teams in the standard setup are weird and don't have all the financial capabilities of regular teams.
As to the results, this doesn't surprise me a ton (woth the caveat that I have no idea how your league finances are set up).
Let's say MLB were a prom/rel setup. Some Appy League team could be the class of its level, move up and improve a bit, then do it again. By the 3rd promotion or so they probably haven't had time to develop players commensurate with their level, and they may not be able to re-sign players hitting FA. Which leads to a big collapse and relegation, and maybe another one, and then they start over.
And no, an MLB team getting relegated repeatedly doesn't surprise me so much. Several MLB teams serve teeny markets or are run like a 2-bit AA team that produces talent and sells it/can't/won't re-sign it. Cincinnati and Milwaukee, for instance, are small cities and absent the real-life cartel might not have stayed in the majors all these years.
Or think of the 70's A's... 3 championships and then several years of disaster ball that would have seen them relegated to God knows where. Billyball to crawl back another level, then the Haas teams to climb back to the top, and within a few years back to the depths.
As I say without seeing all the financials and roster rules I have no idea, but thise results don't seem crazy.
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