Thank you! I ordered something very similar! Such a GREAT idea!
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Try to get him used to the headphones before going to make sure they aren't an issue. I am working to get my son to like headphones but it is slow going. He had tubes in his ears for years so he always had to wear earplugs for any water activity including baths and he came to hate them. So he is sensitive about anything to do with headphones. I think they are a great idea though! As is the iPod. My son has an iPod touch and it is so nice for him to have (and leave my phone alone since he has thrown it into his pool before

I have read a few people saying that they had a hard time with stroller as wheelchair for a double, but if you have to push two kids there is nothing else to do about it! I don't know what ultimately happened for them. Does your son like to sit in a stroller? It was so helpful for my son. There are some fabulous companies to rent from offsite. They deliver the stroller to you resort and pick it up there too. You may want to consider that.