my 87 Grand Prix has a vortec 5.7 in it, but has been setup to run a carb and a 700r4 instead of a 4l60. I got the car this way and I think it has the original 305 pulley system on it, so I can't tell you if it clears the gearbox or not. The hood does close on mine, but not sure on your application. experimenting , I installed my old 327 in it and seems to sit farther forward than the vortec motor, not sure why... look to see what some of the LS swap guys are doing about the fuel tank/pump situation, as that will be along the same line what you'll need for the vortec swap.
I've thought along the similar lines, and am thinking about the feasability of installing the vortec FI intake and computer onto the old 327, (I already have vortec 062 heads on it) and possibly a 4l60 to add to the reliability...
HTH,
Darin