Cost for upgrades given that they always have bugs. (Adobe)
Release cycles which focus on revenue rather than delivering solid products. (Adobe)
no printed manuals (Adobe)
feature sets which are years behind competitors (Adobe and Quark)
Poor integration when multiple apps are form the same company (Adobe)
Feature sets targeted and a very, very, very small percentage of users (Adobe & Quark)
Tech and customer support located in a non-native-English speaking countries. (any)
Moronic "cloud" delivery of software driven by media hype and revenue greed, not driven by user demands (Adobe).
Lack of customer loyalty. Most businesses appreciate a customer who's been a steady revenue stream for years or decades and they offer those customers special rewards. Not software vendors. They have the "one and done' mindset even though a customer may spend tens of thousands of dollars on their software over their career.
Customer incentives decreasing while software costs increase. There was a time when you received all sorts of goodies for your thousand dollar purchase - manuals, fonts, artwork, t-shirts, a nice aluminum tin with discs, etc. Now you get none of that but the software costs more.
Licensing hoops. I realize piracy is a problem. But has any of the licensing features prevented it? Not from what I see. All it does is force legitimate customers to jump through hoops generally at less-than-optimal times - like with a deadline looming.
Besides licensing models, which is always tricky, my biggest gripe has to do with annoying bugs. We all know bugs are a fact of software, but bugs can waste more designers time then anything else. Now-a-days with YouTube one can quickly figure out how to do this or that without a manual, but when something does not work as advertised, that is a big time-sucker for me, especially on the video production side.