In general, I was always surprised that Willow, Tara, and Dawn never got jobs. Over the course of a coming-of-age kind of show in which a young cast transitions out of high school and college, it's just kind of natural that all of the characters would explore their career options and skills. Add the financial necessity of season 6 and, well, it's sort of mind boggling that Willow and Tara are never portrayed as having worked.
I add Dawn to the list because at 14, it may still have been possible for Dawn to work at a grocery store or something. Even so, she wouldn't be legal at most jobs until the age of 15, and then she'd have shortened hours and increased restrictions until 16. Legally, it would be tough for her to make more than a supplementary income out of jobs like those + under-the-table pocket money jobs until she was 18. That said, a supplementary income would have significantly reduced the financial cost of raising Dawn and given her a sense of purpose, independence, and contribution to the group, as well. Lots of kids do it. Lots of kids pay for their own cars, entertainment, food, gas, etc. and save up money for college. It just so happens that I worked several under-the-table from the time I was 13, transitioned to one above-the-table job when I was 16, and was promoted to a supervisory position when I was 17, and I paid for my own food, clothing, entertainment, and a trip to Europe whilst socking away moolah for college. I'm not saying that grieving Dawn had to do all of that. I'm just saying that had Dawn been even a smidgen more mature and self-reliant, she could have gone a long way toward helping out. instead, she seemed content to be a burden on everyone else and even to steal from Anya.
As far as Willow and Tara go, well, there's not much of an excuse for reaching your early twenties (aren't they 22 or so when the series ends?) and never punching a single time card. You don't just come out of college and get a job! You have to have work experience. Even if they were being incredibly selfish and not chipping in at Buffy's place at all while still somehow receiving enough grant and parental support money to support their lifestyles (which doesn't sound like them), they should have been smart enough to at least land unpaid internships. I always thought it was short sighted of the writers not to have at least referenced their jobs once in awhile. I mean, why couldn't one of them have at least had a student assistant position at the school library (I did that) or one of the administrative offices (I did that, too)? By the time I was 22, I was a married college graduate working as a tech writer for a software company, and I'm no super powerful witch. If I could manage that without the mojo, then Willow and Tara could have managed to flip a few burgers or shelve a few books. The fact that they didn't, well, that doesn't exactly paint them in a very positive light.
