By the time it is all said and done, my trip this May will probably top out at around $5,000. Here's what we're doing:
me, DH, and DS (15 months)
going May 13-19
Staying at the Beach Club (big splurge for me!) standard view (can't bring myself to splurge any more on a ROOM

)
7 day MYW park hopper tickets
Dining Plan
airfare for three (yes, I'm getting DS a seat!)
rental car (I like to have my own wheels)
That takes us to a little over $4,000. By the time I finish buying souveniers, extra snacks for the room, new clothes for vacation, a Segway tour for DH, two extra meals, etc... I 'm sure I will have spent the rest of the $$!!
As for what I'd do if I was you it depends on if my dream was to stay for longer, have more "experiences", or go more "upscale". For me the Beach Club is upscale enough (I'm sooo excited about staying there!). I can't see splurging on concierge or something like that. I just don't see the point. I'd rather spend money on experiences like tours and cruises or more park days. Oh yeah, and dining.