- Technical Support
Does the software meet your user need ‘out of the box’?
- Yes – great! But will this always be the case or will you want to customise in the future?
- No – what is required to build on it to meet your need?
How easy is it to obtain technical support?
- Supplier provides under license
- Ecosystem of commercial organisations supporting product
- Strong online user community 
- Tricky to find and employ niche experts (any FORTRAN 77 programmers out there?)
How long has this software been operating?
- Implying; is this an established, heavily used technology?
- How often are updates released?
- Is support growing or waning?
When will it become a legacy product?
- Who else is invested in it?
- Is it based on outdated or cutting edge technology?
- Legality / Policy
- Does your industry / organisation mandate certain software or standards (e.g. for security, auditing, collaboration)?
- Will you use the software for commercial purposes?
- Within your organisation or externally?
- Will you be redistributing these?
- Will you be charging a fee?
Does the software impose technical limitations on user numbers?
- Will you need to obtain more servers or bandwidth to mitigate?
What are the cost implications of increasing user numbers;
- Will you move to a higher support tier?
- Will your license costs increase linearly with user numbers?
Does the software enable outsourcing of:
- Hosting (e.g. cloud)?
- Maintenance (can you expect someone else to mange this software on your behalf)?