I just got mine (had the deluxe last year), but my friend loves hers. She had a lot more flexibility than I had with my deluxe, which is why I moved to the flex. She was able to go over thanksgiving (thanksgiving day and Black Friday), while I was blocked completely out. Over the summer she was able to go into DL AND DCA, while I was relegated to just DCA. She has had no issues with getting most of the reservations she has wanted. Note that you are only allowed to had 2 days of reservations booked per pass at a time. She has been able to still go for three day trips by butting her reservation up to an open day or by simply booking a reservation for a third day (which is a little bit of a gamble) once day two is over (after midnight).
For your first trip, I would purchase 3 day park hoppers from a discounted site (such as undercover tourist or Ares travel) and then on your third say, switch them to APs, then for your first trip there is no worry about reservations or blackout days, you can utilize the Magic morning AND you can get a discount. I paid $371 plus a $2 convenience fee for a 3 day park hopper with Maxpass through ARes Travel. When I turned it into a Flex AP, they gave me credit for the full $400 (the gate price of the ticket).
Edited to add that my friend has used hers for nearly a dozen trips and she is only half way through her pass time. She has gotten every time she has wanted to go with the exception of one weekend at the end of October.