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Hi Devon,
Great question.
I often look towards web based solutions however, first and foremost there must be some way that I can ensure that they are secure.
I have been in Software testing for 20 odd years, primarily managing web based projects and have found that all clients have 4 base requirements
1. How secure is the software
2. What happens to their information if the servers go down, how easy is it for them to retrieve the information, how long will it take etc
3. How intuitive is it, how easy is it to use
4. Performance of the software
These are the questions I ask, and depending on the response, I will use the software
Regards
Sophie