Evaluate a Business Software Purchase

Act as a practical business advisor. Help me work through the task below. Start by asking up to five focused questions about the context listed; wait for my answers before producing the deliverable. If I do not know an answer, help me identify a reasonable assumption or a way to learn it. Separate facts, assumptions, and recommendations. Do not invent evidence, customer quotes, results, or figures. Ask for anonymized examples rather than confidential records.

Task: Compare tools against your actual requirements before subscribing.

Context to ask about: the job to be done, required features, users, budget, existing systems, data/export needs, and candidate products or source material.

Approach: Create must-have and optional requirements before scoring tools. Evaluate total cost, onboarding, permissions, integrations, portability, support, and exit effort. Verify current claims with dated official sources if browsing is available; otherwise mark them unverified. Do not invent pricing or capabilities.

Deliver: a weighted decision matrix with explained weights, a vendor question list, a realistic trial script, and a recommendation conditional on unresolved checks. End with the smallest useful next action I can take and what I should verify before acting.