The wrong software does not replace manual work; it creates manual work around the software. Evaluate workflows, permissions, integrations and reporting before features lists.
Do not begin with a checklist copied from a vendor page. Describe what triggers the process, which roles touch it, what data changes, what approvals happen and what result marks the process complete.
Examples include multi-branch stock, local payment providers, role-based approvals, offline operation, specific regulatory records or integration with an existing platform. A requirement that is essential every day deserves more weight than twenty optional features.
During a trial, do not only create a customer and an invoice. Test returns, reversals, transfers, duplicate payments, partial fulfilment, role restrictions and the reports management actually needs. Edge cases reveal whether staff will later invent side spreadsheets.
Licensing is only part of the decision. Count migration, configuration, training, integration, support and the cost of process changes. For custom software, include maintenance and ownership responsibilities as well.
If a standard process works, adapting the business to a proven workflow can be cheaper than preserving every historical habit. Custom development becomes more defensible when the workflow is strategically distinctive, integration-heavy or poorly served by available products.