Hi @Mike Manke,
When you say Team calendar I suppose you mean the channel calendar (ELT - calendar) in the screenshot.
To me this is the expected behavior as channel calendar is not actually the group calendar, thus it would not show meetings created in the group calendar in Outlook, but only shows meetings for this channel.
However, channel calendar does store meeting items in the group calendar so this is why Scenario #2 happens.
This link which introduces how channel calendar works may be helpful:
Teams Channel Calendar App Makes Channel Meetings Easier to Access
(Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)
If you would like to add the group calendar to the channel instead, currently there is no officially supported way to do it, while this feature is under development.
Please refer to this following active Teams Uservoice thread:
Include Office 365 group calendar
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