I can comment on the tipping aspect....in every hotel I have ever stayed in, we have tiped a minimum of $5.00 per day. This is the same amount if it's just DH and I or DH, myself, and DDx2...I have found that normally, you WILL have the same housekeeper for the majority of your stay. Yes, they will have their days off etc.. but the majority of your stay they will be the same.
Having never stayed at WDW, I am unaware of what happens at those resorts, however in general, we recieve 3X the amount of towels we need, extra coffee, cups etc... at a Four Points recently, we had a mini fridge..the House Keeping noticed I had those little creamer cups on the counter (used that morning..they were empty)...and when we returned that afternoon, I had a dish of them in the fridge for my coffee the next morning. This same hotel, we had gone down with the DD's to breakfast, and the housekeeping staff was just down the hall, ours asked me how long I thought I would be, I said about 1/2 hour...she said, no problem ma'am your room will be complete when you return...sure enough...extra towels....new coffee etc.
I've always found my DD's dolls, or stuffed animals snuggled under the covers, with their heads on the pillows... Usually one of DD's on one bed, one on the other.
My BIL couldnt believe we tipped daily, but once he saw all the extra's we got each day, he began doing the same. He always thought to leave the tip at the end of the stay- but that doesnt get you any special service!....
Just m .02 for what it's worth
Brandy