Improve these error messages

Errors that say "something went wrong".

Rewrite the error messages in this code so they help whoever hits them.

Every message should answer:
1. What was being attempted
2. What went wrong specifically
3. What the reader can do about it

Distinguish messages meant for developers (include identifiers, values, context) from messages meant for users (no stack traces, no internals, plain language, a clear next step).

Flag any error that is silently swallowed, and any catch block that loses the original cause.

Code:

Refactoring and design calls. Cutting code down, naming things properly, and choosing between two workable options.