Well I got my Jack Skellington today and was spending time trying to find all four of his Toy Box chests and I found something rather interesting.
Start an empty toy box, place a tiny tall terrain block next to it and jump on it, next delete the original large terrain block, if a character chest has not already appeared choose a town person and continuously generate him/her in the empty pit surrounding your small island until your bar is full (this should definitely get the chest to appear). Now that your chest has appeared all you need to do is stand in the middle of the island and follow the below instructions.
If you use the play video option the chest will disappear 5 or 6 seconds after the video is finished and be replaced by another random character chest in another corner of your small island (sometimes it may even appear in the same corner, so pay attention to the character icon as well). You can even cancel the video as soon as it starts to save time.
Once you do find and open the character chest you were looking for it will also disappear in 5 or 6 seconds and be replaced by another random character chest, so you can repeat the process again until you get all the character chests you were looking for.
BTW I am on X360 and am not sure if it works on all consoles.
The below video is in real time and as you can see I unlocked all 4 of Jack Skellington's items in less than 9 minutes (although I must admit I was a bit lucky).
6:05 Item 1: Sally Costume
7:50 Item 2 Halloween Town Jack-O-Lanterns
8:20 Item 3: Jack Skellington Costume
8:55 Item 3:Halloween Town Gate