Yes, we have been to WDW! I was lucky enough to go for the first time in 2008 and have been over a few times since! The trip in May is the first through the 9th which would be the longest trip for us to date. You're absolutely right that we need more than 5 days, so we'll add on to make the full time.
But indulging is so hard! It almost feels like I will waste the good fortune and giddiness of having a free trip if I am going to go and pay a bunch of money anyway, you know? I want to REALLY appreciate it and having to take unpaid time to do so feels wrong.
I'm really sorry that sharing my situation is making you unhappy and giving you the vibe that I am ungrateful. I know very well how lucky I am to have won, how amazing the fortune that it was on my birthday no less, and to have the chance to stay in the Cinderella castle for a night makes me shake all over. I'm still so happy about that I almost have tears in my eyes. I am literally over the moon, but there are adult considerations at play here as well as childish happiness. I would give anything to really be that kid that wins a candy factory and eats with wild abandon without a thought of the stomach ache later but.. I'm not anymore.

Us four adults have limited funds as well as vacation time and it sounds like the majority of people are enjoying the openness of the winners when it comes to planning and logistics. I could come in, scream I WON!!! and dance around and leave, but I've decided not to for now.
If you are going to be blunt than I can too: Two trips in addition to my won trip would be a hardship financially. Sorry but those are the facts of my yearly income. I honestly thought my chances to win this thing were essentially nill, same as everyone else here, so I planned out a vacation I could afford before I got word that I won this thing fair and square. I apologize that my husband and I have no children, and no plans to have children, but last I checked that does not disqualify me as an entrant. You are not better than I nor anyone else in this entire world that does not have children just the same as I am no better for not having them. My parents had their hearts set on the trip I planned for us in May, and are of an age that getting them to understand I can pull off the same trip BUT BETTER in October is hard to get across, exactly the same as trying to explain to a younger kid that waiting 5 months if not the end of the world. I'm not complaining about doing that, I'm just sharing the steps of making this all work out.
TL;DR: I'm sorry you feel that way, I AM very grateful. Please realize that I have not said anything about winning this trip not being the best thing ever for my year and possibly life, and its always just been the question of what to do with the May trip.
Thank you, I certainly hope no one else thinks I'm complaining! I'm so freaking lucky I can't stand it and have expressed to everyone in real life that I hope nothing super awful is in store for me to make up for this good luck! Honestly I would think it would be of some comfort that I am NOT the sort of winner who can just add on to my good fortune with a second trip... I am certain there are families far better off financially than us who have won this... the type who drive all brand new cars, live in McMansions and always stay deluxe (we have none of these things).
Its definitely out of my control, lol! I have to wait weeks now for Disney to contact me about it and was shocked when I was told yesterday that May won't work since it is too soon (the rules say take the trip from Feb of this year! HOW is May too early then?!). The main problem here is that my parents are looking to me for answers and I don't have any. You can imagine what calling your parents and only being able to say, look, I won this thing, which is going to be awesome but it means we have to cancel everything but not yet until its in stone, and yeah I don't know when or what or how much but TRUST ME IT'S GONNA BE AWWWWWESOME!!" doesn't go over very well when your Mom has been really looking forward to something. They don't *get* it. That hadn't heard of this contest, didn't quite believe me when I told them, and if you are the sort of person who DOESN'T have to juggle your work, budget and vacation time when plans change then I am jealous of you too.
I am certain ungrateful winners are out there, but I am not one of them. I'm just a fretful planner and too excitable right now from bubbling joy combating with logistics and difficult elderly parents trying to make all my stars align to successfully curb my information overload. Once Disney calls me, and I have verification that this is booked and really really happening I am going to seriously break down and cry. Truce?