We have 19 weeks before we leave. If I start putting $5 per week on a gift card for him he'll have $95, plus whatever he has now. I think that's MAYBE $40. He had money left over in August, but he spent it in December. I keep telling him that this trip is longer and he will probably find more things he wants, but he flatly refuses to listen to me.

So I guess he'll go to WDW for 16 nights and only have $135 to spend and that will be his own fault! Last August he had $150 for 9 nights.
If I can stay away from the pins I won't need that much souvenir money. I usually buy a shirt or a sweatshirt and several pins. I do want a new baseball cap because mine is starting to get grungy. Still, I think I can manage with about $100. DH hardly buys any souvenirs at all. I usually buy a shirt for him and give it to him when we get home. He did buy a camera strap in December, but he typically doesn't buy anything.