Free GIS software is difficult to use and only for experienced users

That may be true only for some programs where the greatest freedom of customisation might scare the beginner. Desktop GIS applications like QGIS or GRASS are not substantially different from their proprietary equivalents. Some of the server applications are even simpler to use than their proprietary equivalents.

Free GIS software is unreliable and not suitable for professional use

Many large companies and government departments base mission-critical services on free software. There are no systematic demonstrations to support a lack in confidence in free GIS when compared with proprietary GIS, and in many cases, the opposite is demonstrated.

Free GIS doesn't come with any support, training or documentation

There are a number of companies and professionals that provide support for free GIS (including training and the production & adaptation of documentation). At present, these organisations are few in number compared with those providing support for proprietary software, but this stems from the fact that, for now, proprietary GIS software is more widely used. 

Free GIS doesn't offer any guarantees

All licenses, particularly those of proprietary software, state that there is no liability for damage resulting from the use of the software. Furthermore, there is no guarantee of proper operation. In this sense, proprietary software and free software are the same, but considering the savings made by  * not * purchasing licenses, it's possible to ensure effective training and support with adequate guarantees of continuity of service. 

Migration from proprietary to free GIS is difficult and costly

Thanks to data standards (shapefiles, GeoTIFF, etc..) and service standards (see the standards developed by the Open Geospatial Consortium, adopted by both free software and proprietary software), appropriate migration plans can be developed and implemented without any interruption to service, saving considerable resources.

Maintenance is very expensive

Although the release cycles of free software are very regular, it's possible to keep a system up-to-date and in perfect working order by applying continuous updates. As a result, maintenance can be planned and carried out at a cost comparable with that of proprietary software. 

Bugs are not fixed or are only fixed in the long term

There is much evidence to the contrary. In most cases, bugs are solved by the community, for no cost, in a matter of hours. In any way, you can guarantee a prompt solution to a problem and the distribution of an updated version through an appropriate commercial support service.

"Feature X" is missing and it's the most important feature for my work ...

In general, free GIS are very feature rich (proprietary software often lacks features present in free software). In the event that an important feature is missing, it's worth noting that the cost of developing new functionality is usually surprisingly low thanks to the re-use of existing and widely tested components (one of the main advantages of Open Source software).

Free software is always free of charge

Although free software can easily be downloaded from the internet, free software is not always free of charge. Free [as in freedom] and free [as in free of cost] are two separate things. There are many programmers and companies that sell free software, in particular, associated services:

  • Installation
  • Configuration
  • Training
  • Support
  • Quality control

Freeware is also free software

False! Freeware, or software provided free of charge in binary form with a proprietary license, does not guarantee any of the freedoms that are characteristic of free software.

Free software cannot be copyrighted

False! Each product of human creativity, where original, is protected by the principles of copyright. Open Source software distributed under the GNU Public Licence is protected by the copyleft model. Copyleft uses existing copyright laws to ensure that the software and derivative works retain the four freedoms mentioned above and do not turn into proprietary software.

The opposite of free software is commercial software

Wrong. The opposite of free software is proprietary software. A software's license does not dictate whether or not it can be sold: there are many companies that sell free software and associated services.

Sources: http://www.gfoss.it/ - http://wiki.osgeo.org/wiki/Desmistificar_crenças_sobre_os_SIG_livres