H3 - s2
I have owned a CFV 16 and a brace of lenses and currently have an S2. As far as image quality, the 16 does hold it's own and I suspect that the 39 is better. I did shoot the Hasselblad lenses on both the CFV 16 and S2 and found that the S2 imaged pretty much the same with the Hasselblad lenses. BUT when comparing the Hasselblad 80 and 100 lens on the S2 via adapter, to the equivalent Leica 70 that is where the Leica S2 shined as a package.
As far as the difference is concerned, price for one, the H3D-39 plus 80 goes for about $8000 in top condition the S2 used plus 70 goes for about $24,000. I will admit, the Leica lenses are really good, and are about $2,000 more than the comparable ones for the H.
Affordability? Well Hasselblad has Leica beat hands down. You have already shown that you do not have an aversion to buying used and the market for Hasselblad lenses is plentiful and affordable. For Leica, the relative newness of the camera and ability for Leica to produce has kept the used prices high resulting in only a 10% savings over new.
The Leica has the advantage of weather sealing, so a little rain will not hurt it. Shooting at 320 ISO is great, even 640 produces nice images, 1250 is still acceptable but not as good as the Canon and Nikons. If high ISO is what you want/need what about a H4D-40?
Ergonomics and simplicity of controls goes to Leica, it has just five buttons on the back of the camera to control the camera, simple menu structure and user preset functions. There is a dual card slot for CF and SD cards that allow parallel or contiguous saving to the cards. Basically the form factor of a DSLR about the same size as a Nikon D3.
-Al
