I don’t really want to clog up my hard drive with unwanted video and it’s easier to edit it from within iMovie.
Have you considered manually importing only portions of the clips you actually plan to use? Or, if you must import the entire clip, have you considered trimming externally in an application like MPEG Streamclip which will allow you to set frame level in/out points and then perform a "Save As..." operation that stores the select range of frames to an MOV file container retaining the proper flag?
Is there anything I can do from within iMovie to activate the 16:9 setting for these as yet unedited clips, so the same pillarboxing doesn’t happen?
Not sure what you mean by "unedited" here. If the files have been destructively split, the flag is gone and there is nothing you can do about it but re-compress. If you mean they are imported but as of yet whole and still contain their flags, then you have two options. The first is to edit non-destrctively within iMovie '08 and the second would be to do the trimming externally.
This second option is really fairly simple. Just close iMovie '08. Open MPEG Streamclip and load a clip you want to trim. Set your in and pout points, select the "Save As..." option, and store the files in the original Events folder with a new name. I would also recommend you perform these trims in their original time sequence so the "creation" date time groups (Finder attributes) are in time order also. When done with the loaded clip either delete it from the "Event" folder or move it to an archival location. When done with the last clip, close MPEG Streamclip, delete the Cache and Thumbnail folders from the Event folder, open iMovie '08 again, and go get a cup of coffee or tea while the files are re-thumbnailing. DO NOT DO THIS TO ANY EVENT WHICH CONTAINS FILES ALREADY USED IN ANY PROJECT. (I.e., this must be done before you start the actual project editing process.)
It seems odd to me that iMovie is doing this.
I suspect that as the application was originally written as an NLE, non-destructive, "by reference" application, the writers/updaters "overlooked" this facet when adding a "destructive" routine and did not provide for checks of this flag nor provide for copying it re-written segments.