Let me start by saying I am, in general, a good tipper. I believe that people are working very hard to make my vacation magical and once a year, I can splurge, and that includes on how much I tip. (Not that I tip badly at home, just more to the 'normal' level)
I think how much depends on where you're eating/staying.
This is what I have planned for our trip (I know people will think me crazy, oh well! LOL)
We're staying SLC at GF, with four of us in the room. For a deluxe hotel, I don't think 2 dollars per person per day is outrageous, and I'm rounding up to 10.00 per day to save myself the trouble of bothering with all those singles. It makes a 10 dollar difference overall during our stay to do so, but will make a BIG difference to me, in the joy I will have leaving that envelope.
I'm leaving another 5 for turndown service. Yes, that's per day. If they're leaving chocolate on my pillow, they deserve a gratuity.
Maids do rotate at WDW and if you only tip at the end of your stay, your regular housekeeper may have the day off and will miss out on the tip for your whole stay.
I plan on tipping 10.00 to the bellservices gentleman every time they handle our bags: myself and others in my party have lifting restrictions so they will be carrying all our bags, which I figure will number 5 small suitcases (rolling type) and a couple light duffels. Might kick in a bit extra if they're particularly nice.
Towncar driver will get ten bucks, each way, to and from the airport.
I don't know about them doing 'cute things' like towel animals and stuff depending on how you tip, I've heard stories of people who don't tip that get them sometimes and those who tipped every day, didn't. It depends entirely on your housekeeper.
I always try, above all, to speak with the staff and make them laugh at least once a day, that goes a long way to making my stay more pleasant and hopefully, their day a little brighter.
My family isn't rich by any means, we're working class people, but I figure the tipping in as part of the cost of a WDW stay. It is a world class resort, with world class CM's (in most cases) and so I like to reward them.
OH! Almost forgot. In restaurants, we start at 20% and if the service is exceptional, we go up. If the service is bad, we complain LOL. Once it's resolved to our satisfaction, we'll tip 15%.
I can hear the jaws dropping already LOL But this is part of my fun on vacation. As I've said before, I'm weird
Tomorrow we surprise Dad with GF Sugar Loaf Concierge...first time ever!!!
p.s. A side story...my DD did the cutest thing last time we were in WDW. We were heading from the North wing of the CR to the main building for breakfast, and a group of about 8 housekeepers was walking past us, happily chatting away in Spanish. My DD, who is interested in the language and learning it, smiled and said "Hola!" they all laughed, waved and said hola in return. They had a big smile as they went on their way. A little kindness and attention to the 'behind the scenes' folks at WDW made our whole day better, and left us all smiling.