Subscriptions have higher chances of survival than permanent licenses because developers have intentionally deferred revenue. So 6 years from now, the motivations to continue operating the business will be higher by a team selling a subscription at $99/year than a permanent license at $299. This way your workflow relying on that tool has higher chances to survive new operating operating systems, new formats and other forms of obsolescence.

I liked Microsoft Money but it is not anymore around. Had it been Money 365, it would still probably be around.