Personally, I'm inclined to be careful about reaching firm or sweeping conclusions about any of this stuff. The press release by Roland is a snapshot of Cakewalk's fortunes from half a decade ago, and while I suspect things did not improve for the better since that time, I don't actually know. And there is no data that I can find that offers any clue as to the state of affairs today.
It looks, to my eyes, like Gibson was buying Cakewalk for the intellectual assets and maybe the talent, but was not buying Cakewalk for the name or the market cache associated with it. They were going to merge it with Tascam, and let Tascam's brand be the face of the company. Something changed, however, and the idea was dropped. Hard to know why, but there could be an entire host of reasons, running the gamut from fair to foul.
As for Cakewalk itself - who knows why the last few years worth of decisions were made. Could it have been a cynical attempt to hoover as much money out of a loyal user base as possible before the company drove off the cliff? Sure. Could it, instead, have been a desperate attempt to keep a beloved product afloat by taking a daring chance with the revenue model? Yes. With either approach, the results would look the same to us, but the underlying reasons are polar opposites. I don't know enough about the folks involved to make even a slightly educated guess about any of that. All I know of Cakewalk's personnel are the responses I see on the forum, and the press releases from the website. I do get the distinct vibe, however, that the folks who worked there really did love their jobs, were invested in the product and the long-time employees devoted a lot of their adult lives to developing it. And I get the sense that they were well respected in the broader audio technology industry.
Like a lot of folks here, I'm heartbroken that Cakewalk -- which I have used for 20 years -- is seemingly done. But I'd guess that those who worked on it for so long are hurting more than we are. They just saw a career's worth of hard work and personal investment evaporate overnight.
There are way too many unknowns to reach any firm conclusions about, well, anything. I think it would be best to reserve any conclusions or condemnations until more information comes our way. Eventually, it will - either from Cakewalk's remaining folks, or from other news and industry sources. The Roland press release I found struck me as an interesting glimpse into the scope and scale of Cakewalk's finances and value as a company -- something I didn't even have a clue about. Considering all that is going on, its very intriguing information. But I don't think its nearly enough to give us any real insight to what has happened since.