I keep getting conflicting answers and I'm still unclear...the only official answer I've gotten states that there is no specific landmarks to reach, rather you're picked at random based on time played and involvment in forums. I am still confused because what I've been told by VIP's is that they got it simply on X amount spent.
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https://communities.glu.com/tap-sports-baseball-2019/discussion/5453834/the-unofficial-vip-guide#latest