Architecture Questions:
Application: Is the application SOA oriented?
Does the application provide standard authentication mechanisms? (profiling, groups, roles, LDAP integration)?
Does the application provide monitoring and tracking of the operations executed?
Is the application certified in terms of security, vulnerability or external illegal access?
Does the application include profile restrictions mechanism to prevent access to sensible data?
Does the application allow internal development through native mechanisms (API, SKD)?
Does the application include new releases and updating schemes?
In what programming language is the application developed?
Does the application include data quality control mechanisms?
Does the application manage information life cycle mechanism?
Does the application include information tracking?
Does the application include a data dictionary?
Does the application include a data model?
Does the application include graphical and documentation of such data model (if such)?
Does the application have a documents management mechanism, for structured and unstructured data?
Does the application include a reporting module? Capability to configure and generate reports?
Does the application include a Business Intelligence tool, ratios, and metrics for business analysis?
Infrastructure:
Does the application run in virtual environments?
Does the application run client servers architecture?
Which applications servers are supported by the application and what versions?
What web browsers are supported the application?
Technical requirements for application server (memory, processing, storage)
Operating systems supported by server?
Operating systems supported by client?
Operating systems supported for database?
Replication/backup schemes for software and hardware?