My question was close to the mark for the reason why, but not quite. After reading through blog after blog, tutorial after tutorial, I finally found one that gave off a hint of what might be happening.
Locked home screens. The keychain tutorials always left the accessibility settings for the keychain blank, so it would default to Apple’s lowest/safest access level. This level however doesn’t allow keychain access if the user has a passcode on the lock screen. Bingo! This explains the sporadic behavior and why this only happens to a small percentage of users.
One line of code, solves the entire mess.
[wrapper setObject:(__bridge id)kSecAttrAccessibleAlways forKey:(__bridge id)kSecAttrAccessible];
Add this line where I’m setting the username and password values. Works like a charm. Hope this will help someone out there. It confounded me for quite a while until I was able to put the pieces together.