Where I am careful
When rules are cheaper than a model
Plenty of “AI” requests collapse into a lookup table, a validation script, or a change to who is allowed to approve a document. I will say so in the first week. You still get a written note and a bill for the time it took to find that out.
Data that must stay in Singapore
Some records cannot leave the country. That constraint decides the hosting, the model choice, and whether a hosted API is even on the table. I design around the restriction you actually have, rather than promising a stack and discovering the restriction later.
Cost per request once the desk is busy
A prototype that looks cheap on twenty examples can become a line item once it runs all day. I keep a cost log beside the quality log from the first harness run, so you can see both numbers before you agree to scale.
What software will not repair
If two teams disagree on the meaning of a field, a model will amplify the disagreement. If nobody owns the exception queue, automation will fill a folder that nobody opens. I write that down in the scoping note so it does not hide inside a demo.