If you have unlimited money for camera, sets, camera stabilizers, crew, film, and post processing then 35mm film is just better; wider dynamic range, shallower depth of field, natural color reproduction, true 24P, longer lenses (because of larger format) and what have you.
On the other hand, something like the Arri D-20 (HD 4:4:4 RAW) has been used by high end film makers to do things they say (I have only read about this) are nearly impossible with film because the nature of RAW processing allows them to "develop" each shot in post processing to adddress issues that would have required more time and attention in camera if shot on 35mm film.
I know there are no "stupid" questions, but I hate hypothetical questions, because if you have unlimited funds, the choice is more a matter of preference, what your DP is familiar with, and the circumstances of the shoot. Some movies had to be shot on smaller digital cameras because the camera had to be portable, for example.
The real answer to your hypothetical then is, once you've finished pre production, you find a DP that is really good and suites your project, then let him/her use what he/she knows best, because knowledge of the camera counts for more than anything.
Now, I must get back to the real world and do real work because I need real money to pay my real bills. Read Creative Cow or Film Maker Magazine, and you'll find lots of articles about big names DPs and their transition to high end HD cameras, with the pros and cons of shooting with a specific camera compared to 35mm.