... How do you tell the difference between "giving in" and "spoiling"? How do I know if this is okay, or too much?
You'll know when he's 30. Up until then we're just guessing.
Eldest daughter and eldest son are only a year and a half apart and have gotten the same teachings about money from the git go, but eldest daughter saves her money and always has, while eldest son is perennially broke. Now he's got a "real job" working on computers a few days a week, and he pretty much spends every cent as fast as he makes it.

Mind you, eldest daughter makes her Halloween candy last from one Halloween until the next.

.....
Personality has at least as much influence as parenting, IMHO.
My brother and I are very different, or...were very different, with money as well. He made Halloween candy go to Easter, and Easter candy go to Halloween. Little stinker. I snarfed mine much more quickly. I seriously think that candy is a great way to determine what's going to happen in the future with money!

(though you have to remember the parental influence with that...hubby kept his, but that's b/c his mom MADE him...as soon as he was in charge of his candy, he ate it all up. Same with money. While under mom's influence he was decent with it; once he was gone for the final time from her place, he went crazy with it)
We don't even go every year to WDW, but the fact that he talks about it like we should just be able to go tomorrow is making me second guess our plans on purchasing DVC.
But why? I don't understand.
I *like* that my son feels safe and grounded enough, with trust and love for hubby and I, so he can feel safe and secure in the concept of us taking a vacation in the future.
Do you know how much I would have LOVED to be that safe and secure growing up? Now, GSU had it way worse with her mom...mine was just run of the mill broke parents, abusive-to-mom dad, early divorce, no child support, weird dad, etc etc...but kids growing up in environments where you CAN'T count on anything have it way worse, IMO.
My son thinks that we can run down to California at the drop of a hat. He understands money fairly well...but he doesn't understand how far away it is. I remind him that it's 4 hours in a plane to San Diego, and he remembers that, but he doesn't remember the *feeling* of the long-to-a-kid plane trip. He WANTS to be there, he wants to see his uncle and aunt and their cats, and have the possibility that his generous and successful aunt will insist that he and I go to Disney for a night (happened once, in summer of '09), and because that's what he wants to be true, he ignores the fact that it's far away (relatively).
Just because he asks to go often doesn't mean there's anything wrong with it; just means he likes it!
Do you think this spoils kids if they just expect the family will go?
I don't think one aspect of life will "spoil" anyone. Vacations, when a person can take them, are lovely. It's *nice* to be able to anticipate a nice vacation. Way better than not having them, or having junky ones (oh yay dad, we get to spend our week with you fixing your truck? AGAIN? oh, work called you in b/c there's no one else, so we have to spend a full day sitting on a Greyhound bus, when you know one of your kids gets carsick? gosh, it happens so often it's almost like you don't tell work that you have your kids...).
It's hard combating entitlement at this age-- he wants everything he sees. That's normal for a 4 year old, right?
It's so normal that to put the new meaning of the word "entitlement" onto it is an insult to 4 year olds, IMO.
4 year olds want everything. Some grownups want everything (even when not given everything!). I've just described my son at 4 and a bit earlier and beyond, and also my husband. Going through downtown Disney at
Disneyland was MISERABLE when they were in their "I want" phase. Worse, when DS said "I want", DH wanted to give it to him! We started staying OFFsite simply so I didn't have to walk through that mall again.
But...DS outgrew it, DH became more understanding of the ways of the budget (once he threw off the after effects of a far too controlling mother, and the after effects of his rebellion from her), and we can walk through the disney mall without me wanting to go home. Whew.
The part that was especially hard for me was when we would buy DS something (feel free to substitute DH in here, too, he was just as bad, and for longer, and for more expensive "toys"!) and *with that item in his hand* would ask for something else.
IN a way, we're extra lucky that we've gone so relatively often, because I didn't just despair that DS was "spoiled"; instead, I got lots of chances to talk to him, explain how it made me feel, etc...and then a matter of months later, I could see how the behaviour changed. And it did, over time, as he grew out of that phase.
DS is a saver in many ways. He *loves* all of his toys, and we still have some of his *baby* toys because just as I'm about to donate something, he'll play with it again. The other day he told me some very specific things he wants to give away, and they have been the same items on that list for awhile, so I think we'll be safe to do it. He's not the "I want that" just after he got "this" kid anymore (unless he knows that he's getting outfitted, say, as Ron Weasley on a Universal trip...then he knows he's getting a robe and a wand and even a rat). Just happened, over time.....
But who knows, maybe at 30 he'll be robbing banks so he can go to Disney...I doubt it, but it's possible. I'll keep having talks with him, hopefully he'll see that that's not the best way to make money.
