I've been told by my manager to favour off-the-shelf solutions - he feels it will allow us to hire more easily if I decide to leave. I prefer not to have the hassle of writing software myself, or downloading and configuring often very complex software which might not be that polished. Sometimes, I just want a support person to call who can fix stuff quickly so I can get on with my work rather than dealing with support issues. The people I work with are not very tech-literate so I need software which even they can use easily (otherwise I just end up doing their work for them).
There are many products I would never consider buying, and many top-rate open source products I cannot live without. But if you can encapsulate your expertise and knowledge in software and sell that to me and make my life easier, I will cheerfully part with money.
Your mileage may vary, but I have found that many free solutions offer some of the worst support in the world. Even worse if you are trying to use their software in a way that they hadn't intended.
That can't work for everything, sadly. I know that products that centralize all of your communication, like FogBugz or Flowdock, make one hell of a difference, but it's hard to demonstrate that centralizing communication is helpful if someone doesn't currently believe that.
Around here, until you hit the 5-10K mark, it is as good as free. (Not that I condone such wanton spending.)
