A Company is not your friend.
Either it don't depend on the money, in which case the progression of a product relies on their passion. Or it needs the money in order to stay alive and grow as a company.
Cakewalk is not for example, Cockos. It's a company relying on revenue and income. It has to pay its employees. They don't gift something. There has to be a financial reason to sell lifetime licenses with the prospect of never ever again charge for the progression of the product again.

How will cakewalk pay its employees then?
What IS this reason? The current offer generates a short term revenue stream. What's the long term financial prospect?

Forgive me being skeptical. May be you, or cakewalk itself, can shed some more light on the future of cakewalk, one if its product the chose to not gain more revenue long term.

As much as I like this offer, from a customers point of view, I can't see any advantage from a company's point of view, which will have an impact on the product from a customers point of view.

Thanks for your insights.

Auuuuggh.....Nooooooo - not again! Someone far less polite and professional than Craig might say that Cakewalks financial plan is none of our *&€£ING business!  Buying platinum does not make us company directors. Take the deal or continue to look a gift horse in the mouth. The choice is yours. It's either $99 or $199. We are not talking sheep stations here!
 
Red wine + forum = ranted. Sorry.

Not being Craig, and playing devil's advocate (because I am usually critical of Cakewalk these days), there are some legitimate, although risky, business plans that can involve such an approach.
 
For example, look at it from the perspective that a DAW is a platform for other music-related tools. These tools are mostly VST effects and instruments, but can also be bolt-on features like drum replacement, pitch correction, vocal alignment, etc. Assuming you have a modular architecture where it's possible to plug these things in quite easily, you could give away the core DAW with the hope that users will buy future add-ons to use with it. Who knows, maybe 3rd parties will be encouraged to develop for the Sonar Platform and there will be a mini app-store of addons. Maybe someone will write a better Staff View, for example. The users who need notation will be able to buy that, everybody else pays nothing for the feature, Cakewalk will take 30% of the money, and everybody's happy. Perhaps.

Lifetime Updates are available for purchase only until August 31st, 2016. Not a permanent solution.

TabSel I can't see any advantage from a company's point of view, which will have an impact on the product from a customers point of view.

no insight to cake particularly, but this kind of action usually means the company needs a quick injection of cash to see them through to delivery of something(s), and that something(s) is (are) expected to then pick up the cash generation

One thing that seems to be getting overlooked is that Cakewalk is not dependent solely on the income Cakewalk alone generates.

Cakewalk is part of Gibson, and Gibson are not a small company living hand to mouth.

Cakewalk's strategy has, I suggest, to be considered as part of the strategy of the Gibson company as a whole and that strategy might include using Sonar as a way for other parts of the company to make money. Much as Apple sells a very full-featured and highly developed DAW for less money than any other similar products because people wanting to run Logic specifically need Macs, and an inexpensive but fully professional DAW is a way to persuade people new to digital audio to buy Macs.

1) The lifetime upgrades are ONLY for Platinum. They'd still be selling memberships for Artist and Pro (and supposedly Artist is actually their biggest seller these days).
 
2) This offer only lasts until the end of August. Then it will be business as usual.
 
3) Many of the people who have been dumping money into the flagship year after year already have all the included Cakewalk doodads and are likely getting hesitant to upgrade EVERY year (just want fixes and enhancements). This makes some money and keeps long time customers happy and focused on Cakewalk. I am one of those people.
 
4) Cakewalk sells other items that apparently make them decent money. By keeping people who may have been drifting away (like I was) in the fold they are more likely to be aware of those products and new products and hopefully buy them.
 
I seriously don't see what doesn't make sense about this. You just have to think it through a little further than "ZOMG!! IS FREE 4EVA!!"
 
As I noted in another thread Cakewalk/Sonar is also a great direct marketing vector for Gibson brands which sells all sorts of doodads for musicians. Even if Cakewalk only breaks even but drives sales in other departments that seems like a no brainer for Gibson.

no matter how you slice it or dice it, it's chump change for what you get.
I've been paying cakewalk on average $100 per year for about 16 years.  
that's $1600.  $2000 max.
That will get you 1 quality piece of outboard gear or high end mic.  
For that same amount I have had my own complete recording studio in a box for 16 years.
 
Everyone has the option to buy it once and keep it.  Old versions of Sonar still work very well.
But if they are going to keep developing it and adding more functionality, I am happy to fund their efforts. 

OP - I wouldn't worry. Lifetime updates won't hurt Cakewalk.
 
Many people will buy Synths/Upgrades/Pro Channel stuff from Cakewalk with the $$$ they would have spent on memberships. 

Why does Craig or any of us need to spend time on this? Most if not all forum members understand basic business concepts. We got a great deal offered to us, enjoy. Don't worry, be happy.