I've noticed, like you, that managers and others often avoid "Free" software. I think it's a result of a couple of factors. One is simply perceived value. If you don't charge for it, people don't think it's worth anything. The other factor seems to be accountability. If you've paid big bucks for something, you (theoretically) have some sort of claim in case things don't work. Of course with software, most of the time get nothing of the sort, but you don't find that out until you try to collect...

I have a different theory on this. Its related to how large company "enterprises" function. A manager who is responsible for the WebSphere contract controls a considerable budget and is perceived as being a powerful person. Even better that manager has virtually no responsibility for the delivered product, except if it is a success. If the product sucks then the vendor screwed up and the manager is off the hook (this is especially true if the source code on the vendor product is closed). If the product rocks then the manager is congratulated for a good job done. With free tools the manager has no large contract to manage, reducing their perceived power in the organisation and has no vendor to blame their problems on. Instead they and they alone are responsible for the success or failure of their project. Considering how little time managers tend to stay in their roles, and the potential loss of income for being held responsible for failure it is no wonder that most senior managers avoid technology whose failure can be laid at their door.

In a lean and hungry company the id guess the rules are different, presiding over a large budget external vendor failure could result in serious problems for the company (such as bankruptcy) and the manager responsible will most likely be held to account for presiding over such a costly failure. Whereas a failure of a project whose only costs have been headcount and development time is most unlikely to result in serious problems for the company and thus the managers in firms like that are much more likely to take advantage of free solutions that provide them with low cost solutions.

The basic issue is how the company holds those responsible for these decisions to account. In most large companies failure is almost never the responsibility of the senior managers involved (witness CEO's receiving massive payouts for being responsibile for serious losses in their companies), smaller companies without the protection of huge capitalisation and the cover of large organisations have to take a much more realistic approach.