It really varies so much by field, how much the degree matters. And within that, even the company. But, IME, having a degree gets you above the first "line" or "hurdle," like PastryGoddess mentioned. Also, as I mentioned with my friend Adam, his company policy said that people with a degree start at higher pay, and can max out at higher pay, than someone without a degree, even if that someone has been working there longer. I don't think this is an unusual policy.
A lot depends on the individual still, though. I mean, you can have a four-year degree and be a total jerk with no work ethic who can't hold down a job for more than a month, you know? And I also know several people, especially in computer programming, who never got a college degree but hold down great jobs, because their field/company values skill and experience over schooling, and they are responsible, hard-working employees.
Personally, I value full-time college starting right after high school, and that would be my default. But, if it was looking like I really couldn't afford that (for myself or my child), I would look deeper into my (their) career interests, and see what that specific field was like--if it was a good return on the investment to take out loans, go part-time, etc.. I'm in the sciences and a lot of college kids get summer internships that connect them to companies, who then snap them up as soon as they graduate and will even pay for further schooling. The internships often only take kids who are currently enrolled in college and then hire them only when they have the degree, so if you aren't in school (usually full-time) you miss out on that. I think you just have to do some serious research first about which strategy would be best for you/your kid.