NO EXPERT HERE- lol.
but I have a Disney reservation for later in December and every page of my itinerary says "check out by 11" is that what you are seeing?
the giant tickets thread seems to indicate that a 4+1 ticket is plainly just marketing and to Disney's system is it a 5 day ticket period.
You say 10/24 to 10/29. When I count on my fingers that's 6 days. Yet you have a 5 day ticket. You didn't book any FP's on the 24th did ya?
it should let you make a fastpass on your checkout day anyway as long as you had enough days of tickets, so not allowing 10.28 wouldn't have anything to do with it showing you as checking out that day anyway as near as i can tell.
If you can't figure it out you're going to need to read one of these giant thread to get the phone number for Disney IT. They can log in to your account and look at exactly what you would see (I've had them ask me- is it OK is I log on to your account to look at it?)- so they can see what you do and let you know if that is wrong.
also - seems certain days have had issues at times- probably you should read the October thread to see if the day you are having problems with is common issue.
I did do fast passes for the 24th, but that's my first day in the World and would be my first of five days, with the fifth being on the 28th. I am not booking anything for the 29th, as I'm leaving that morning, and wouldn't be going to the parks. I'm holding for IT as we speak - the CM I spoke to at Disney said that this is a common problem, and she transferred me right away. Thanks for pointing me to the October thread - I will also check there!