Usually Cakewalk does not release until near the end of the year, so I don't think a new release is coming that soon.
As for if you should get it, well if you are asking me, then I would say yes, only because that's what I did a few short hours ago!
I guess I would calculate if the 99.00 was worth it if say, we were expecting a release NLT December 31st. That would mean that for about $11 a month spent NOW, I can play with new cool features like Melodyne integration, Addictive Drums and new effects and a whole lot more. Looking at that cost from an entertainment perspective, that's about the cost of movie ticket here where I live (Southern USA). Now, I've seen some good movies, and some bad ones as well. So, I reason the cost -- I could spend $10.00 on a couple of hours on a bad movie, or I can spend at LEAST a couple of hours per month on the latest version of my DAW, making bad music

but having a GOOD time. To me, the choice is a no-brainer. For you, depending on your budget and needs, it might be different.