It'll be tough but, if you're both into it and cooperate, it could work. Playing a dungeon crawl sort of game would be easier than figuring out how to do something with a more complex story line. I've played countless games of Chess and Squad Leader against myself...but have never tried to wrap my head around something this complex.
I think, you'll end up (if successful) with basically a cooperative story-telling sort of event than a standard D&D game and that's cool and fine. You could try the route of making up some basic event/plot/encounter cards and draw from those decks when you feel it's appropriate.
Let's say you start with the premise that you're in a tavern (natch) and hear a scream outside. There's a dead body there. You investigate and do well on your checks. What happens? I think you work together to come up with a clue that seems reasonable given the circumstances. Then you follow that up...he died from poison so maybe it was the local thieves guild. Go investigate, which triggers somebody's alarm at some point because you fail a bluff check, which leads to a fight in an alleyway with a couple of thieves...and so on.
It actually sounds like fun to try. I've got a group with three long-time DMs who switch off running different games...and this is something we *might* be able to pull off together. Not an easy thing to do, I suspect...and it'll probably take some experimentation.
Good luck with it! Oh, and let us know how (and what) you do.
M
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Wow, so much to say about this topic...
Firstly, I just wrote about a DMless covert ops game I played. I'd played it with Warhammer 40k origionally, but I've also tried it out with the Pathfinder Beginners Box and it worked well.
Then check out SoloNexus on blogspot. He's done great things using Rory's Story Cubes: look for the "9 questions".
TinySolitarySoldiers took this further with an easy little system that I really love.
I hope someone finds this helpful.