Distinguish common work from distinctive work
Some needs are shared by many businesses. Others depend on a particular operating model, handoff, or information structure. Describe the workflow in plain language before comparing products. That gives you a basis for judging fit.
Test an existing product with real scenarios
Use a normal case, an exception, and an incomplete record. Ask the people who will use it to carry each scenario through. Notice where they need side notes, duplicate entry, or a separate spreadsheet. Those workarounds are part of the real cost.
Connect when the tools already do their jobs
Replacing a useful product can add migration and maintenance work without improving operations. An integration may be enough when the main problem is information moving between tools. Confirm API access, data ownership, error handling, and export options before relying on that connection.
Build when the workflow warrants it
Custom software is worth considering when the process is important, existing products create persistent workarounds, and the business can support ongoing ownership. Budget for maintenance, user feedback, monitoring, and changes after launch.
Compare the whole operating cost
Look beyond the subscription or initial build price. Include migration, training, duplicated work, integration upkeep, support, and the cost of leaving later. Write down the tradeoffs and the conditions that would make you revisit the decision.