Renewal Price

Why don't you let the new user pony up the $105 dollars with the bait that'll be half that when it renews?

Since most sales of Quicken Classic are renewals, what you're basically asking them to do is slash the price of Quicken Classic, as almost everyone would be paying the lower rate your suggest. Well, that's just not likely to happen. They've been raising the price over the past decade because the selling price times the volume of users from back when Quicken was part of Intuit did not generate enough revenue to continue to invest in improving the program. (Note that "improving" includes making changes/fixes behind the scenes which simply maintain working functionality, not just new features.) Of course, every user would welcome lower prices! But I just can't imagine they can go back to pricing from a decade ago while maintaining their staff and services.

As for discounts to new users, that's a typical marketing tactic to try to entice new users to try the product; some will try it and not renew, but those who stay will pay full price going forward. If they can't grow the user base, then either the price will go up more, or they'll decrease work on the product leading to its eventual demise. It's been clear for a while now that Quicken Inc. sees Simplifi as its long-term future, as its online-only, works-from-anywhere, platform-agnostic approach mirrors most cloud based software services. As long as enough people keep subscribing to Quicken Classic, they'll continue to keep it alive, but their marketing makes clear that Simplifi is where they see their future growth.