No one asked, including anyone from Cakewalk, but here's one way I'd like to see this happen.
DISCLAIMER: I have no idea what Cakewalk has in mind, I'm just throwing out an idea here. Suppose I'm in Rapture Pro and browsing the Guitar presets. I see a folder with an asterisk called "Gibson Les Paul 12-String." This means that something new is available but not installed. I click on it and see a dialog box labeled "Gibson Les Paul 12-String Expansion Pack" with three options: More information, Remove, and Not Now (in case I want to check it out later). If I choose more information, it takes me to a landing page on the store with audio examples, a description, and an option to buy.
Or the dialog box might say "Free Gibson 12-String presets available for download, happy holidays."
Something similar could be done with updates. For example, I go to the browser and Melodyne has an asterisk. I right-click and see a dialog box that says "Melodyne Version 5 now Available." If I click on more information, I'm taken to the store with update pricing and specs. Remove takes the asterisk away and leaves the old version intact. Not Now leaves the asterisk to remind me there's an update available. I would find this less intrusive than Melodyne opening my default browser and constantly reminding me V4 is available, which I'm not ready to install yet because I have V2 Editor and while V4 is nice, I don't want to step back to Essential and lose the Pitch Modulation tool.
The mechanism for in-app purchases could also be used for updates and freebies. For example I still come up with FX chains, even though they're not included in the Rolling Updates any more (if they're included in Rolling Updates, users have to download the Anderton Collection each time just to get one preset). I could donate the preset and people could get it for free...or not if they're not interested.