Thanks for testing this out @manuel and for the questions.
I didn’t know the answer to this either, but I looked and figured out roughly why. We recently introduced a distinction between classic plugin outlets and wrapper plugin outlets, in this PR from last year: DEV: Allow PluginOutlets to 'wrap' a core implementation by davidtaylorhq · Pull Request #23110 · discourse/discourse · GitHub
The wrapper plugin outlets are the ones that allow only one connector, the rest allow multiples. To illustrate, the current core plugin outlet code is this:
<PluginOutlet @name="custom-homepage">
{{#if this.currentUser.admin}}
<p class="alert alert-info">
{{i18n "custom_homepage.admin_message"}}
</p>
{{/if}}
</PluginOutlet>
and it allows only one connector. But if I change the core outlet code to:
<PluginOutlet @name="custom-homepage" />
It will allow multiple connector templates just fine. We could make this change in core for this particular outlet, but this difference is more general. It does feel a bit opaque to developers, though, I see your point there.
Note also that multiple connectors have an ordering problem, afaik we don’t have a mechanism to decide on ordering.
I think the best approach here, regardless, is what @merefield suggested: use one template and then reference Ember components from it.
Default alert is only shown to admins, FYI.