Tiny 11 VM weird?

I would say, Not at all. If it works for you and gets you what you need, that is the only thing that matters.
I might express concern about Memory allocation for photo editing in a VM. That may take a little research and tweaking.

You might look at QEMU for running the application.

Yes, Photoscape has dependencies on .dll's and API's not well supported in Wine, especially the later versions. I think avoiding a compatibility layer really is your best bet.

Alternatives to GIMP include Pinta (I use the latest and it works well), Krita, Photopea (Online browser based) - You might explore these without the pressure of needing them to replace Photoscape, given your method of using it as you outlined. They may give you a quick editor you can use natively and explore, falling back to your preferred and comfortable Photoscape as needed - pressure free.

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