I don't actually carry any gift cards in to the parks with me. That is why I use my KTTK card for everything. I know if I lose it I can walk to guest services and have the old one cancelled and a new one printed. I don't have to worry about trying to replace gift cards. My gift cards stay in my room and I charge to my KTTK. The night before check out I go and get a print out and compare it to my reciepts but you could go every night or every other night if it is more comfortable for you. This gives me a chance to check for wrong charges and get them fixed before I pay for them. Then I go to the counter and give them my gift cards (in this case it will be a $500 one) and pay off the charges to my room so nothing gets charged to my room. I like not having to carry by debit card or gift cards to the parks. I have one card to carry for each of us and I use that key all day long for fast passes, to pay for food and merchandise and for my dining plan so I know immediately if it is gone. I track my expenses very well so I don't over spend and I keep all of my reciepts in a zip pouch that attaches to my lanyard with my card and the kids' cards and the fast passes and my photopass cards. This may not work for others and is just how I prefer to do it. I agree that you have to do what feels comfortable to you otherwise you will be a nervous wreck the whole trip worrying about things. I also like that it doesn't cost me anything to get the $500 card. I have always done $200 at a time before which came in 2 $100 cards. This was fine but after the last time that I had a hand full of cards and the desk lady had issues getting the application of that many right I decided just to go for the big one this time! I will probably cry when I finally have that $500 baby in my hands LOL!