I'm wondering if you can select
a Classic application as your default app
to open a type of file? (whatever happened to the good ol' file exchanger)

Yes, you can. Select a file of the type you want to specify for. Get Info. In the "Open with:" list just select any app that can handle the file type. The OSX apps are at the top of the list, the OS9 ones underneath a dividing line

Specifically, I want PhotoShop 5.0 to be my default photo editor.
But, when I select a jpg file
and go to Get Info
Select PhotoShop 5.0 as default app
Select Change All
  I get a dialog asking me if I am sure that I want to
set all my Adobe PhotoShop 5.0 files to open with Adobe PhotoShop 5.0.

Well, of course.
You'd think to be asked if all .jpg files were to be opened with ...

The same happens on my iBook with Panther. Must be only a little bug in the dialog box, because when you click Yes it all works - at least for me.

But, APS never does get to be the default.



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