Steven Zahm@ Jennifer
RE: Is there a way to automate the WP account creation for each user? For example, for a directory of 500 entries, would a WP account need to be manually created for each user’s entry?
Sorry, no, there is not … that said, you could export the entries using the Email export tool and use that with a CSV bulk user import plugin to add all the users.
RE: After their WP account is created, what happens if their email address is used in an Organization entry as well as an Individual entry? Are they linked to both, or just one?
The linking only occurs when the user logs in. In the event that there are multiple entries which contain the same email address, the user will be linked to the first entry that the database returns as a match. After a link has been made where or how often a duplicate email is used because it will remained linked to that single entry, it will not get linked to multiple entries.
Hope I have answered your questions thoroughly!
ps. failed user login lockouts are temporary. It is in place only to help prevent brute forcing.