In regards to your first question, it could be a date issue for the infotype record. If the records for open enrollment are set to be effective for a future date, and the current record is delimited, then you won't see it in the open enrollment screen. This is true for benefits like a flex account because they have to be re-elected every plan year.
Let's say that any elections made in the current open enrollment period you are in take effect June 1, 2014. If the current record has an end date before June 1, then in the enrollment screen the employee will not see the current record because SAP is looking at June 1.
Take a look at the employee's record and at the benefit you want them to see and see what the end date is for the most recent record.