For the past ten years the yearly family trips ended and my wife (then girlfriend) funded our trips. We do split pay duties, as she has a bank account with direct deposit and I get paid cash, so, I have a mattress. She usually gets the tickets and gas, I pay for food, souvenirs, and spur of the moment things (unlimited dining at Sea World, quick queue at uni, animal safari at Busch Gardens...things of that nature). We have the benefit of having a fairly effecent travel vehicle, live 3-4 hours from property, and family in the Orlando area to stay and eat with when not in property. The most expensive thing we pay for is tickets.
I also have a large family, three grandmothers, 8 cousins, six aunts and uncles and my mom and brother. When we make a bi yearly trip, we roll 22 deep and counting since my brother just got married to which he gained a step son and another is expected in October.... Somehow, everything seems to get paid for before we ever get into talks about the family trips, I pay gas to go down, I supply my own beer (I'm the only drinker), snacks, and I take my mother and wife somewhere nice to eat while in Orlando, usually fishbones because I know a chef there. Truth be told, I don't enjoy the bi yearly trips nearly as much as our frequent weekend runs to orlando. Its taxing to be involved in a group that large. Someone is always upset because they missed something or are tired, and as much as I love my grandmothers, pushing them around epcot, dhs, then mk in a wheel chair is by far the most exhausting thing I've ever experenced. I would much rather pay my own way with just the wife, and enjoy the best things of central Florida at our own pace. But, having pizza with my grand mother as we walk around world showcase and she tells me stories of her and my late grandfather's travels in Just about every country represented, is something I cherish.