One of the biggest issues is Mac-only. Some people consider the Mac the only "real" computer for music. Although the market share of OS X is about 8% in the general market, estimates in the music industry place it at between 50% and 65%. Samplitude, Acid, and Mixcraft are other Windows-only programs...they don't get much attention either, and the Windows version of Digital Performer hasn't gotten much traction. (The exception has been FL Studio, which sells very well, but it's a very different kind of program.)
Windows is perceived by the "Gearslutz mentality" as not a serious solution. Therefore, anything that runs only on it is not a serious solution...guilt by association.
Advertising in magazines is not the answer because people who are prejudiced against SONAR will not be swayed by an ad. People are swayed by experiencing it. Much of SONAR's marketing is "in the trenches" at the store and distributor level (some of those people are clueless about SONAR, and actually dissuade people who want to buy it). For example, you'll see ads for SONAR in Sweetwater's catalog. You'll also see Gibson's product specialists in stores evangelizing the salespeople at, for example, Guitar Center. Cakewalk just did a big press event and store tour in Japan, where for whatever reason SONAR does very well. "Big in Japan"
The music industry is slow and conservative. The membership program has been out for about six weeks and the push will continue. Of course it also doesn't help when a forum has thread titles like "SONAR BROKEN!! Automation DOESN'T work!!!!!" and it turns out to be pilot error, but there's nothing that can be done about that.
Also note that more and more companies
do have SONAR on their radar. Universal Audio used to pay no attention to it but does now. Nektar's Panorama keyboard has a SONAR template, as do more keyboards and controllers. Finally, SONAR's sales keep increasing steadily, mostly from new users as opposed to "switchers," which is where "the rubber meets the road." I think part of that is because of the perception that Cakewalk is no longer in danger, and is here to stay. Marketing efforts will continue and expand, because if nothing else, they're having results.