I once worked for a well-funded nonprofit where those in charge liked to buy fancy things and sort of "show off" technologically. Given needs were met with over-the-top solutions, and while it was fun to buy and play with the gadgets, many of us regretted the monetary waste and frequent additional support effort that these extravagant designs required.
But the biggest IT pain point was a long-standing history of nontechnical people making technical decisions, including software build vs. buy decisions. These decisions were rooted in a budgetary turf war: One department's budget = their decision. And at times the tech staff was never consulted or even brought into the loop as to what decision had been made.
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One such example proved to be a colossal headache to an important group of people. The tech need in question was a way for the administrative assistant to be able to transcribe board meetings on her computer while still remaining at her desk, and preferably in real time. What about getting her a fancy laptop? Well, the company policy was that laptops were reserved for only those who traveled as part of their jobs, and the board members didn't want the administrative assistant in the room for the entire meeting. What about getting her a headset so that she could conference into the meeting? Well, that was too practical.
The solution involved buying a fancy audio device that would record audio in real time to MP3 and save it on CompactFlash memory cards (for archival) and a radio transmitter for the real-time aspect. This particular buy was made by the facilities department, as it was considered a core building asset.
All of this gear was installed by a local high-end home theater company (they also designed the sound systems for local stadiums and concert venues), and it was beautiful. This board room would have made a James Bond villain proud: LCD screens that would electronically motor up from a side table, speakers and microphones discretely installed all over, and touchscreen controls for everything.
The central problem was that the radio transmitter was able to be set for a variety of frequencies and was surprisingly high in its broadcast strength. The signal needed to go maybe 50 feet, but instead, it covered many miles. This was a security problem that went undiscovered for about a year, and the board, who liked to be clandestine, were unwittingly broadcasting themselves all over town. I didn't even know the transmitter had been installed until the day the fire department showed up.