microsoft/winforms-designer-extensibility

Will the designer always be ran out off process?

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Or is the plan to one day bring the designer back into the Visual Studio process?

I don't believe that'd ever happen. Consider, VS is running on net472 and your project targets .NET - the designer has to run out-of-proc. Now, it's plausible to consider that one day VS may run on .NET, then .NET Framework projects have to run out-of-proc. Not to mention the present scenario - VS is a 64-bit process, and your .NET Framework project requires 32-bit support...
And once you have both version of the designer running out-of-proc, then there's little to no incentive bring those in-proc.

That makes sense, thanks for the insight. This really helps me understand some of the challenges you have had with the designer and is very interesting.

Very much so. Of course now I have some ideas and will keep playing with this to see if I can come up with anything useful.

I've never built a custom control before, and don't have experience with the designer. But if I can, I'll try to get up to speed and implement something similar to what is described in IDragSourceHelper::InitializeFromWindow Remarks.

The DI_GETDRAGIMAGE message allows you to source a drag image from a custom control. It is defined in Shlobj.h and must be registered with RegisterWindowMessage. When the window specified by hwnd receives the DI_GETDRAGIMAGE message, the lParam value holds a pointer to an SHDRAGIMAGE structure. The handler should fill the structure with the drag image bitmap information.