This entry over at IT world discusses some of the forces behind users that fully intend on using an open source application and make the jump over to the proprietary software world instead. It seems counter-intuitive that any user would will give up something that is free just to pay for it. But as the entry states, there are many reasons users do this. Open source applications tend to have a lack of support, lack of features, and lack of documentation. Oddly enough, there are some open source applications that share the same qualities as their proprietary counterparts. They both have a great feature set, documentation, etc. But like all software, the subtle differences can simply make one application better than the other.
The biggest stumbling block is installation and initial configuration of open source applications as far as I'm concerned. Proprietary installation and configuration procedures are generally a more enjoyable procedure. This is the first step to using any application and is important to get right because it gives the user an impression of what the rest of the application experience is going to be like was it actually gets installed if ever.
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