This is going to be a long-winded rant, so feel free to skip it.
I have an AutoCAD user. Up until about 4 months ago he was running AutoCAD 2008 on an XP box with a dual-core processor and 4GB of RAM. Then he started complaining about crashes. I wasn't able to replicate them, but his machine was a little old, so I replaced it with a quad-core/8GB Win8 box. Within a week he is complaining of crashes that he is actually able to show me. Fair enough, AutoCAD 2008 isn't officially supported on Win8, so we drop a ton of money on AutoCAD 2014. He still complains of crashes, and that his computer isn't fast enough. Just a note- AutoCAD 2014 is installed from a download. A 38GB+ download that needs to be extracted locally before install and takes nearly 100GB after install (requiring nearly 200GB locally free during install). Because of these size requirements I'd switched from a SSD to a 3TB drive. After his complaints I dropped in a 500GB SSD. Still complaints. I swapped his machine with an identical system used by a co-worker. Co-worker had no issues, this user still complained. In total, I've replaced his hardware 4 times and re-installed from scratch the OS and all software 3 times. All his "rejected" computers are now in use by his co-workers without complaint. I'm about to take one of my monster workstations and reconfigure it just for him (i7-4770, 32GB, Titan, 500GB SSD). If this doesn't work I may need to employ Coug, his basement, and his special services.