(I usually lurk on this thread, and rarely post anywhere because of time constraints, but hey, its WORTHY!
I am going to agree with Zebra15--how much money does he have saved up for school? My kids have always expected that they would have to pay for school itself--I've been more than willing to help with some stuff, but it really is on them.
Here's how it has worked so far for us. First, since we live WAAAY out in the country (twenty minutes from any town that would have work), I have maintained a kid car/insurance for them. ONE kid car, so for the year or so of overlap, they had to figure out sharing, as well as ferrying their younger siblings around to various events/jobs. You guys are lucky in that your kids can just walk to downtown for work, yes?
So, oldest DD got her licence late--17 1/2, but was working (lifeguarding) before that, we'd just give rides. She ended up homeschooling all the way through, worked her way through various Red Cross skills (she's a WSI instructor), then decided to do her Basic EMT training, then her Advanced. She bought her own car three years ago (at 20yo). She now works various EMT jobs, house-sitting, and garden/cleaning stuff with me. She's living at home (we have encouraged this, since she's got so much overnight work, it makes no sense for her to spend money on rent when she's not there very much). She doesn't pay rent, but is constantly helping with rides, grocery shopping, little-brother stuff, farm chores.
DD#2 was homeschooled until halfway through 8th grade, then went to high school. She did sports (both school and year-round swim team, where she worked as a lifeguard), and worked (lifeguarding and cleaning/garden work). She's now a sophomore in college, majoring in civil engineering. She has gotten substantial scholarships, but has paid for the balance herself--within a week of being at school, she got a job, and works several shifts a week in the dining hall. Since I saw how hard she has worked, and is willing to work, I have continued to pay for car insurance for her so she can work when she's home. I also pay for her phone.
I've got DD#3 headed to school this fall as well--she's the same age as your E, and she's expected to pay that sort of stuff, just like her older siblings. She's also doing sports, and is pretty busy doing extra-curricular stuff (she also decided to attend high school). She is on vacation this week, and was begging me to bring her to work with me, lol--I clean for various people, and at one job, there is often "extra" work to do, so she came with, and we cleaned together for a couple of hours. It is really nice bonding time, actually.
I think it is important for them to have to WORK for stuff, otherwise it is too easy to feel a sense of entitlement. They are on the cusp of adulthood, and really need that push sometimes!
ps. It is good to "see" you again!