So this topic picked up again during my trip and I have my own $.02 to add that I do not believe was mentioned.
On the whole, I agree that redesigning DDMS, while neccesary, may not be profitable. However, there is A LOT of info on DDF that can be helpful to any (not only a points/cc) kosher traveler. Including this content in an easy to navigate DDMS would IMHO increase traffic and perhaps make that redesing profitable.
The content I am reffering to is spread out throughout the various dest guides and TRs. AFAIK, there is no (good or popular) website for the kosher traveler. However spread out throughout the various dest guides is all the content neccesary. Besides for all this valuable info, there is also a plethora of interesting/exciting TRs. I believe the inclusion of these into DDMS would DEFINITLY increase traffic. Heck, half of DDFB posts are about questions that could be easily answered if this info was accesible to the "Hamon Am".
Now, I know we can say again and again, "Just look it up its all on the forums", but the reality is most people are (legitimately?) afraid of DDF. Including this content in a redesingned DDMS would be a valuable asset. I honestly believe that if done right a sister-site with this info could be just as popular as DDMS.
(Not the best written argument, but I think it gets the point across)