Well, my boss made the unfortunate decision to "upgrade" our Quickbooks Pro from 2010 to 2014. This has lead to a series of nightmares, which I'm about to rant about.
I practically begged my boss not to make the switch, as I don't feel Intuit deserves our money (Quickbocks is expensive), since they develop proprietary/non-free software. Because of this, there's no way of knowing whether or not this software contains spyware-like functions. Hell, I know this software employs DRM to enforce a strict one-computer-per-license policy, so using spyware to restrict protect the policy (by means of lawsuits) just seems to make sense.
That said, my boss's biggest reason for upgrading was because, according to her, "every few years, some of the services stop working". Does anyone else smell timebomb-activated antifeatures, or is it just me? Ultimately, we're just trading old damaged goods for newer damaged goods.
Immediately, we had trouble accessing the old files, as they were stored on another computer (our corporate server), in a network folder (mapped as a drive). This was a good way to to things, as the server was backed up every night. This also simplified the process of allowing multiple computers to access these files at the same time.
However, for reasons I can't understand, Quickbooks 2014 doesn't want to play nice with this setup. After countless hours of troubleshooting, we eventually managed to move the files to another location, and set up that location on the network. This most have taken my boss at least two or three days to solve (with her insisting that I'm not allowed to help, even though she asks me for advice for every other computer-related task). TWO OR THREE DAYS!!!
Then, there was another two or three days overcoming the multi-user licensing, as she and I both tend to use the program at the same time (on different computers). Apparently, the $240-ish CD only contains one license. Buying a second license is so expensive, it's literally cheaper to buy a second CD, than to buy an additional license. However, Intuit was too stupid to anticipate users accessing the same files using two copies of Quickbooks from two CDs. I don't know what the exact problem with this was, as my boss insists that this problem wasn't "any of my business" (right... the software most of my job depends on isn't my business ). Eventually, we got desperate enough to contact customer support, which meant spending a huge chunk of time on hold, followed by letting some Intuit support "expert" (who didn't really know what (s)he was doing) access my boss's computer remotely. Somehow, by some miracle, (s)he got things working.
In the time it took to simply install the software onto the HDD (never mind the time it took to make the software actually work), I could have downloaded a GNU/Linux distro, and installed it to several computers. I guess there were plenty of (large?) files to copy off the CD.
Then, in addition to mass code-bloat, I got many of the same glitches I had experienced with Quickbooks 2010, such as vendors temporarily disappearing from the vendor list. I guess four years wasn't enough time to fix such glitches, although they did have time to create a reinvented GUI (that nobody actually wanted).
So, to summarize everything, the software is expensive, glitchy, won't access files stored in "certain" folders, suffers from an absolutely horrible DRM system, presumably enforces DRM with spyware, and requires huge amounts of HDD space, all without actually add anything new to the table. We had to endure all this to temporarily escape from the harmful effects of damaged goods.
Personally, I was hopping to use these problems as an opportunity to convince my boss to make the switch to Free Software such as GNU Cash, but my boss could care less. The only Free Software she uses is Firefox. Otherwise, she insists that "Free software can't be good, since it's free". When I try to explain that I'm not referring to price, but she usually interrupts me in mid-sentence, telling me that she doesn't want to hear anymore of my "nerd talk". Oh well... she was warned.