Whether acquiring software initially to solve an unmet need, or considering replacement for an existing, but inadequate solution, here are several ideas to consider and evaluate:

• How would conversion to the software happen?  For example, can data be initially loaded via spreadsheet, or must it be entered manually?
• Can data within the system be easily downloaded into a usable format for analysis within spreadsheet programs?
• What are the ongoing maintenance costs, considering (a) licensing, (b) hardware, (c) vendor support?
• To what extent does the software integrate with others that you may be using, such as accounting programs, scheduling applications, email, and text messaging?
• If the application handles credit cards, is it compliant with PCI (Payment Card Industry) standards?
• What is involved with adding users?
• How are upgrades handled?
• To what extent is the vendor willing and able to enhance the software to better serve your work processes?