>> The consideration for context-menu for me is particularly intriguing, as there's
>> a lot of functionality already included in Org's context menu.
>
> This is not right. I think you are confusing ordinary menu bar and
> context menu. Context menu is "right click" menu that will display
> different items depending on where you click. Org mode currently does
> not have context-menu-mode integration (we should fix this deficiency)

Maybe it's some third-party package I'm using, but right-cliking on an Org
buffer gives me a lot of options:

<https://0x0.st/XF1y.png>

>> I don't often use org-ctrl-c-ctrl-c, but now that I've seen the interaction
>> menu for properties as an example, I'd say the best option for it would be
>> which-key, as it's a simpler menu.
>
> My conclusion so far is that there is no "best" for every user. We
> should ideally support user-customized menu UI. The main question is how
> to do it.

I also agree with this conclusion. Hope others can contribute with
suggestions of how to go about it.

>>> This UI flow can be implemented using context menus, which-key popups,
>>> transient menus, and also using embark (where the way menu is displayed
>>> can be customized).
>>>
>>> All the 4 approaches represent different UI models with various
>>> strengths and weaknesses:
>> ...
>> It has options for setting the pop-up type and position. Could this help with
>> flexibility?
>
> May you elaborate what "it" refers to?

Sorry, seems I forgot to clarify. "It" in this context was referring to which-key.

It has the following variables for altering (window) display:

- which-key-popup-type
- which-key-side-window-location