Submit a new version of my paper if my supervisor only commented on an old, very different version? As a PhD student, I face the requirement to publish at least one of my papers at one conference from a defined list of conference. In late November, I submitted a "draft version" of my work to my first and second supervisor. 

In mid-December, I received feedback from the second supervisor. The feedback I received affected mostly writing style, making it appear more like a concise journal article instead of a book chapter suitable as part of a final PhD thesis, etc.

Since the holidays, I worked on my paper substantially, implementing ideas and criticism from befriended PhD candidates as well, and could send a new, final version to my supervisors Friday. My fist supervisor now explicitly told me that he read the first version of my paper, and now he wants to give me feedback, most of which he believes may have been included in the second supervisor's feedback and hence addressed in my new version. 

However, he cannot give me feedback before Wednesday due to time constraints on his part, not even a phone call. Instead, he stressed that the first paper is not ready for submission.

I am now facing the problem that the submission deadline for the journal is on Tuesday. Hence, I must choose between 


skipping the deadline and not submit anything, 


which would be undesirable. Although there is nothing preventing me from choosing a later conference, the message this would send to my environment (and myself) about my work standards, communication flow and time planning would be demoralizing.


submit the renewed version anyway,


without my first supervisor having approved of it (the second supervisor promised to still give feedback in time). I submitted the draft, with two months left to the deadline, to identify problems with the general direction, and I knew it was not ready for submission. The fact that the differences between the draft and the current, polished version are very large now tells me that the current version may be very well suitable for publication, even in his eyes, if he read it.

Essentially, my possible errors here are:


submitting a paper that, even in the second version, is bad.
not submitting a paper that would have been perfectly fine.


Regarding the first error, how strong is the effect of having been rejected from one journal or conference, as to not being allowed to submit to other conferences work that was already submitted once before? The research field is the intersection between management and corporate finance.

Is there an effect on my, or my supervisor's, or my university's, reputation from submitted a (potentially still by far sub-par) paper--after all, this should be anonymous?

Furthermore, there could be a negative effect of my supervisor feeling undervalued if I meet him Wednesday for feedback on a paper (although not the same paper) that I submitted the previous night. However, my supervisor is quite pragmatic, and I am sole author of this paper, so I am convinced he would understand my reasoning--but also the possible negative effects I mentioned above.

Regarding the second error, I would lose time, the opportunity of valuable feedback, and disappoint my research group, as this conference was defined as my submission target past summer already; all this over underestimating a possibly quite nice paper.

Edit:
I saw this question, and want to stress that I honestly believe that my paper is not incomplete, and could be published (but then again, I am just a PhD student in my second year).
Ask your second supervisor to talk to your first supervisor about it -- they may be able to agree between themselves that the feedback from your second supervisor alone is enough, given the time constraints.