Look, I understand that most people here are musicians and don't understand how marketing, pricing, etc. works so let me explain.
There are two important elements to consider:
Customer acquisition and in the case of anything requiring renewals,
customer retention. Customer
acquisition is extremely expensive.
Failure to retain customers (commonly called "churn") is also expensive. Therefore whenever a company is dependent on renewals from discretionary income (magazines, satellite radio, etc.), they will make significant efforts to retain customers. (Of course, companies like utilities where you
have to buy their services every month don't offer discounts, and besides, most of them are regulated monopolies anyway.)
A really good example is magazines. A magazine might cost $8.95 on the newsstand, so there will be blow-in cards that offer "6 months for $19.95!" or whatever. Well, that's a good deal and helps with customer acquisition. The magazine won't make any money from it, but the gamble is that the customer will like the magazine and subscribe when the six months run out.
At the end of that six months, the magazine has to convince the person to re-subscribe or they will fail to retain the customer, and thus have to do another pricey customer acquisition if they want to avoid churn. So you get an email offer that says "renew now for a special price of [whatever]." This is intended to provide an incentive for people to re-subscribe.
If they don't, it's equally likely that several months later, they'll get a "we want you back" promotion. And so on.
Cakewalk not following through on their explicit statement that they expect to run specials and discounts from time to time would fly in the face of everything that's known about renewal-based revenue models, including what the company has done for 30 years with updates from one version to the next.