2012 was the year when I bought the most proprietary software licenses.
Such purchases were mostly prompted by special needs that seemingly could not be answered by available free software.
I bought a license for Infix (PDF editor), for Abbyy FineReader Express and Readiris (Japanese and English OCR), for Antidote (French spelling and grammar checker), for Pdiff (visual comparison for PDF files), for Kaleidoscope (visual comparison for image files) and for Transform (XSL transformation).
Antidote from Druide is the software that I use the most often, after OmegaT. I could not work without it.
Infix from Inceni comes as a very distant second. I use it on some PDF files that I need to translate as PDF. I export the contents to Infix export format and translate that file in OmegaT thanks to the Infix XML filter that was developed a while ago. Infix does not come without problems (crashes, clunky user interface), but it works most of the time.
Abbyy and Readiris were bought when I needed to OCR a few important files, sometimes PDF, sometimes plain images. I then translated the exported files with OmegaT.
I bought Kaleidoscope from Black pixel because I needed to compare a set of multipage PDF documents. Kaleidoscope does not support PDF, but I thought I'd be able to easily convert the files to a compatible image format. That was not the case. Even though my machine is quite powerful, I could not find a practical way (free software or not) to convert two 400 pages PDF files into a single image file with a good enough resolution to process the file set in Kaleidoscope.
Then I bought Pdiff from Csci. Since there was no trial version, I asked the developers to try it on my file set and send me an excerpt of the result. What they sent me was very satisfying, but was made in the "pro" version that had an Export to PDF feature for reports, while the "lite" version had nothing like that. I bought the lite version anyway, but its report function was nowhere close to what the pro version offered at a priced that did not justify a purchase (999€). There is no way to export the report in the lite to anything useful and there is even no way to copy it for conversion to a different format.
Eventually, I did the comparison with diffpdf a free software from Mark Summerfield. diffpdf has a problem: it does the comparison page by page but does not notice when data is spread on 2 pages. To fix that, you have to manually add white pages in places where you want diffpdf to do a dummy comparison so that most of the pages are kept in sync. This is slightly cumbersome but took only about 1 hour to complete on the 400 pages x 2 pages set. The resulting comparison report in PDF was easy to read and exactly what I needed to proceed with my work.
Transform is from Neil Lang, an individual developer. I was being lazy and I wanted something more than what XSLPalette offered so I checked the App Store and found Transform. I paid the license, installed it, tried it, send a request for feature to the developer who promptly answered by telling me that the feature was already there, but "hidden" from the eyes of the user. After playing with it a bit I decided to use xsltproc on the command line to proceed with my work.
I learned 3 things:
1) Free software ended up being good enough for what I needed and I wasted money on software I did not really need.
2) Good proprietary software does not come in "lite" and "pro" versions. Either it does what you need it to do, and it does it well, or it is not worth bothering.
3) There is a business selling software output when users don't want to buy a license to a software they'll use only once every few months. I could see myself spending a few (dozen ?) euros on a nicely output PDF comparison report, or on some nicely OCRed files.