If the user decides not to enable pretty permalinks, then I would respect their decision not to enable them.
Two potential options:
- Simply state that the Plugin requires pretty permalinks to be enabled in order to work
- As a fallback, just append the keyword as a query string if pretty permalinks are not enabled.
EDIT
Perhaps try this tutorial for extending the WP rewrite rules?
Basically, the rewrite rules are an array, so you crate a function that pulls in the array, manipulate it, and then return it; then you hook that array into the generate_rewrite_rules
hook.
You might also reference what the WP Access Control Plugin does.