How much should I adapt a paper to fit another conference than where I originally submitted? Me and my research buddies have written this paper, summarizing and drawing conclusions from a proof-of-concept we've coded and tested. This paper regards several fields or subjects in (applied) Computer Science, and fits relatively well the call-for-papers of a few highly-rated conferences. On the other hand, former papers on the same subject have been published mostly in a single conference, and only a few in one or two others.

We're a bit overdue on submission; and the most-relevant conferences' next submission deadline is in about half a year or never (one may have been discontinued, it was more of a workshop). So, we want to submit to a well-regarded conference, with a matching CFP.

Now, while the CFP covers our work, the conference's 'angle' is somewhat different. This while other papers on our subject build a sort of internal discourse amongst themselves, i.e. essentially pick up the discussion where other papers left off. More or less. This is obviously made more acceptable, or maybe made possible, by the fact that most of them are published in the same conference.

So my questions are:


Is it a good idea or not to try for the upcoming conference, even though we'll be the first paper on our subject to be published there? i.e. do we stand a reasonable chance?
How much should we try to adapt the paper, to sound less of a continuation of the 'internal discourse' of our subject and more likes something appealing to the 'crowd' of the upcoming conference?


PS - The results are sound. They're not the end-all of exploring the subject, but there's plenty of meat in there. So it's not a borderline-accept paper (if I can say so myself).
It's very hard to judge how well a paper will be received by a particular set of reviewers (which is the real question for paper acceptance).  It is certain, however, that the more that you adapt the paper to speak to the community that you are sending it to, the more likely it is to be well received.

I think that in making your decision, you would be well advised to think less about time and more about audience. Six months isn't very long to wait for a publication, so unless you've got a reason to really hurry, I wouldn't take that as a primary factor.  Instead, consider whether the work you are doing is an incremental step that would be best reserved for discussion in the focused community or whether you think it's broad and interesting enough that the larger community should hear it.  

If the former, then finish the paper now and set a reminder in your calendar for a few weeks before the deadline of the focused conference. If the latter, then go for the earlier conference and put in as much work as necessary to speak to the broader audience.  Don't just send a narrow paper to a broad conference, though: even if you get accepted, you will have less impact than if you adapt the work for the audience to which you are intending to present it.