ArcGIS Pro

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Price Model: Annual subscription, including the web services, reduced price for individuals and non-profit organizations.

Runs on: Windows

My favourite aspects: The help system, Model builder (a graphical tool for doing complex analysis), integration with mobile app for data collection and 3D visualization tools

Best for:  beginners and advanced users

Alternative: QGIS

Short description: Desktop GIS app with almost all the functionality you ever will need and in a modern UI and a fantastic built-in help.