Usability is atrocious and if you do not use it all the time you have to google the simplest things (for which the results are mostly outdated or wrong or bad practice so you have to be careful with which explanation you follow) which the software itself could explain to you.
100%. Freeze all work on crypto except for fixes for new problems that show up. All rest of money goes to hiring a UX expert for a design that anyone can pick up for common case and then implementing it.
Even trying to use a bash script to automate things is tricky because of gpg2's interactivity. I'm sure it was put there to improve usability, of course :) (which it does, in the interactive case).
Presenting such a complicated technical topic only in it's purely technical form is not enough imho. Clear and concise explanation for each and every action and item that gets displayed (and the whys!) would do wonders.
> This money will firstly allow us to continue our maintenance of GnuPG. We also intend to use it to fund our work on the Gnuk security token. And, one new project that it will support is a book called "An Advanced Introduction to GnuPG." A book for developers who want to integrate GnuPG into their programs, and need to understand the various concepts, the important security tradeoffs, and common pitfalls; for digital security trainers who need to understand GnuPG to be able to make sound recommendations to users; and, of course, for enthusiasts.
I agree with waldfee that it would probably be a very good idea to invest a chunk of that money into UI improvements. GnuPG is not exactly the friendliest program out there, even for those of us who are very comfortable doing everything from the command line.
It seems like things that were sponsored by major organizations because they saw the good in having their name associated with a product or service in favor of getting the "internet at large" to pay for things that have become ingrained as "But it's free so why should we pay for it?"