> * I (like most companies) have a variety of unstructured and/or immutable logs. I can't just DROP FROM table WHERE. Is it acceptable to delete this data by waiting a few days for a retention period to expire, or do I have to retrofit deletion functionality in?
In order to be allowed to store PII (even if it's in logs) you need a specific purpose. Why do you put PII in logs? What benefit does the user have?
> * What if the retention period is a week, or a month? What if I've been advised to establish those longer retention periods for other reasons?
If there is a legal requirement to keep PII (for example accounting) you can/must keep it as long as the legal requirement demands. If there is no legal requirement you have to delete PII, there is nothing that trumps that.
> * If a bug is found in the data deletion workflow, is it an undue delay to say we'll tackle it next sprint? Do we need to drop everything and make it a priority now?
If your next sprint starts 1 month down the road the regulator won't be happy. If it's next week and your GDPR doesn't have other gaping holes a reasonable regulator won't bat an eye.
> * Once we've resolved a personal data deletion bug, is it an undue delay to roll it out slowly over a week? Does it matter if this is our standard rollout process, or if there's a risky hotfix process we're deliberately choosing not to use?
Are you playing for time or doing responsible software development? If a regulator thinks you are bending the rules good luck, otherwise nobody will demand of you doing dangerous stuff.
I know, there are a lot of things open to interpretation. But as my lawyer told me: "There are people getting a speeding ticket for 5 above the limit and others who don't. Try to stick to the limit and make sure you are seen as one of the second category."