MLO Lite Might Do It!
Maybe I answered my own question. MyLifeOrganzied light version seems like it just might do the trick. Simple, light, free, transportable on a disk. This could reduce the complexity (obscurity?) of GTD implementation in Outlook to zero, allowing Outlook to be about what it should be about-a calendar and email!
The only major hurdle seems to be the requirement that you buy the pro version AND the pda sync app to make carrying MLO on your phone possible. You'd think they would make the PDA apps compatible with the light version and pick up the addition $15 in revenue from users like me, instead of forcing us to look elsewhere, or go papered with portable lists...