- I'm wordy. Feel free to skip to the bold part, below. -
Our family has strange circumstances, admittedly. DH and I have a young son together, but we both have kids from before (17-y-o twins, for me; a 13-y-o singleton, for him), who all live with us.
The twins' dad & step-mom live nearby, are very involved, and extremely wealthy. They'll buy the twins pretty much anything they want. However, if I anticipate things and ask them to hold off for birthdays or Christmas, or not overshadow something I gave the twins, they will. They're not intentionally out to "spoil" the kids, but buying whatever crosses their minds - at the moment it does - feels normal, for them.
The twins are somewhat Autistic, have learning disabilities, and unrealistically assume that, as adults, they'll live in mansions, drive Cadillac SUVs and own every electronic device the day it comes out, just because. Many teens fantasize about such lives, but most understand there's some connection between wealth and a good education, hard work, and some amount of good luck. My kids really don't understand that, and I feel like it would be good for them, if they did.
Our 13-y-o has a non-custodial mother who lives far away and is trying to regain custody (which she lost when he was only 8). She hopes that when he reaches the magic age of 14, he'll help her by testifying that he wants to live with her, instead of us. She promotes this, in part, by giving him crazy amounts of spending money. And she does this in a sneaky way, which encourages him to be sneaky. She lied about his age, to help him get a checking account with a credit-backed debit card. He buys things online and either has them shipped to friends' houses, or to her, then she mails them to him under the guise that they're gifts from her, so DH and I aren't allowed to have opinions about the goods.
In many cases, what DSS buys himself is nothing we would complain about, anyway. So the pervasive attitude that he needs to keep his purchases a secret from us is really offensive and creates the impression there's something wrong with what he's doing, when there isn't.
Other times, he's just inconsiderate. For example, he asked DH and me to buy him a new iPod for his birthday (and had every reason in the world to assume we would), then he couldn't wait and bought one for himself, two weeks beforehand. As parents, we feel we should be able to discuss with him the rudeness of that, and the value of delayed gratification. The financial dynamic with Mom makes that difficult or impossible.
With ALL THREE kids, we struggle between "Should we let them buy whatever they can afford, with 'their own' money?" and "If the money they're given vastly exceeds a reasonable allowance for their ages, or what they'd be capable of earning, if they were paid what their labor's actually worth; then it feels irresponsible to let them spend their teens being accustomed to buying themselves $150 tennis shoes and iPhones...things many hard-working adults - including DH and I - can't afford? Aren't we setting them up for major disillusionment and dissatisfaction, when they actually start supporting themselves, as young adults?"