My neighbor is an attorney that handles their licensing contracts (came in as part of an acquisition). He is quite impressed with the licensing process/infrastructure, but I wonder if that's the problem: the processes are set up for major deals with huge licensees and, as a result, the individual gets screwed.
Try to find out what the licensing is for Creative Cloud.
I spent a couple of hours on their help forum - which is manned (and womanned) by frustrated users and some adobe employees (probably contractors) who don't seem to understand the questions.
I finally succeeded in finding a pdf document containing all the terms and conditions in N (where N is large) languages. No index, toc, or hyperlinks. English language (actually attorney-eeze) was way down in the doc.
Ordering isn't the only thing Adobe has screwed up. Their CS6 documentation has no index nor table of contents. I've wasted hours simply trying to find answers to simple 'how do I . . .' questions.
This is a real startup opportunity - if you can negotiate the IP nightmare.
That's been my view on things. Not that I know your neighbor, but... for a company that has that much marketshare, they concern themselves primarily with catering to getting large amounts of money from larger companies. They've optimized for the fewer use cases, and seem to not understand there's a larger audience who'd be willing to pay them money if the process was easier (even at current prices).
I'll have to ask him about it.