I don't know, lots of people bought the Roland V studio . Also Roland recording interfaces and keyboard controllers. I think much of that was A.Because they were already Cakewalk users and B. The V Studio was a nice piece of hardware.
See the splash article in SOS 2008.
HERE Unfortunately Roland sold Cake and left v700 development. To this day the V Studio can be made to work albeit not without some work in newer setups.Lots of people still using this hardware. Once again, I don't believe Roland gave the profit cycle enough time to develop. If they had rode through the storm they might very well be sitting in a similar place to Yamaha. JMHO The quad capture probably sold better because it was aimed at the bedroom musician and sold for less.
And I agree, they just made a bunch of bad moves. Most you already mentioned. I personally liked the skylight interface and I think that idea would have flown much better if they would have bug proofed it better before they launched it. The combination of bugs and a new GUI killed away those who loved 8.5. By the time X3 came around it was too late. Many had already decided they didn't like it which is sad because X3 was a stable program for the most part.
the iOS port is likely what happens to an idea after it goes through upper management. It probably had good beginnings and declined from there. I'm guessing management wasn't really listening to what they worker ants were trying to say ...or didn't care.
The idea that legacy functions somehow choke a program is not a totally proven concept. Coders work around issues all the time and the software works just fine. Much current software runs on older code. I do agree that the code kept them from a good iOS port. The last example of Sonar is still on my computer humming along nicely.
In one sense you're subscribing to any software that has a yearly release. It just isn't called that. You still pay to upgrade or continue development. At least this is how I see it. I think the word "subscription" scares people away. Even though Cake was careful not to call it a subscription.