Despite the fact this discussion keeps turning up like a bad penny, from a legal standpoint, I don't think there would be a problem if you took the approach that the Over Flanders Fields (OFF) crew did. They created an excellent WWI flight sim that is an addon to CFS3. Their work has pushed the envelope of what can be done with CFS3, greatly improving it in many respects, but avoided any copyright issues. They even charge for their latest version and don't run afoul of MS. So, if your "rewrite" is basically a super addon, I think you are OK.
You would need to identify what you want to do and who your target audience is. Are you talking about a free super addon as I described above or a commercial product. Either way it would be a lot of work for little return. And, as mentioned in earlier posts, who would do it? Although we are still seeing new members join here, new addons, and new websites popping up, I suspect in sheer numbers we do not have a huge following. A faithful one, but probably not large enough to support a commercial endeavor.
Don't get me wrong, some of us have been flying CFS2 for over ten years and think it's the finest WWII flight sim out there; certainly the most flexible and open to modification. In fact, that is probably why it has managed to sustain interest over all these years; just about the time you think you've seen everything it can do, someone comes up with yet more great stuff. The problem I do see is in the age and overall design of CFS2 compared to the current state-of-the-art in flight sims. Newer sims like Rise of Flight, Wings of Prey, and Cliffs of Dover have almost movie quality graphics. Maybe those sims aren't as open to modification as CFS2, but they have tremendous appeal to new simmers brought up in a world of CGI. I think anything done along the lines that you describe is really preaching to the choir and would appeal only to existing hard-core CFS2 fans. Maybe not worth the effort.
Rather than a "rewrite", if something was going to be done I'd like to see someone take the Best Of The Best of the existing addons and combine them into individual all encompassing downloads, one each for the ETO, MTO, and PTO. A player (new or old) could download a single file containing all of the best scenery, airfields, planes, ships, effects, campaigns, etc. that are already out there and instantly have a complete theater of operation. Of course whenever you talk about what's "best" you're being very subjective. Perhaps a small group rather than a single individual would be the best way to decide. But again, who? The biggest advantage to this I think is that it could be accomplished in a relatively short period of time. A rewrite would take years. By then CFS2 may be 15 years old or older and realistically there will be very few remaining simmers to have justified the effort.
Just my two cents...