I think as others have said, to an extent it's trial and error regardless of price. It's a case of finding which products suit your skin - what works for me may not work for you. It's a bit like perfume in that make-up behaves differently on different people's skin.
I prefer quality over quantity and tend to buy certain higher end brands that work well for me. Not because they're high end but because they WORK! I have oily/problem skin and I find that cheaper brands just slide off my face. But so do certain expensive brands! Even when I was a broke student, I never got on well with brands like Rimmel. Tried Maybelline but it slid off my face. I had some success with Boots No. 7 and Bourjois (the rumour back then was that Bourjois was made by the same people who made Chanel's make-up....probably total rubbish but made me feel special at the time).
These days I mainly wear a combination of Armani and Marc Jacobs with random bits of Trish McEvoy, Tarte, Laura Mercier, Clinique, MAC, IT Cosmetics and La Prairie thrown in.
My foundation is Armani (for lighter coverage, cooler days) or IT Cosmetics (for full coverage and/or when I'm going to sweat i.e. hot days or at the gym). I use the matching primer (so either Armani or IT Cosmetics). My loose powder is La Prairie which is amazing but I just found out it's been discontinued (sob!) so I'll probably go back to Armani or Clinique. My concealer is MAC. Always. Best concealer ever. Although I use Trish McEvoy for under my eyes and as an eye base.
Eye liner is Marc Jacobs or Armani. Eye shadow is Tarte (used to be Armani but I suddenly developed an allergy to it). Mascara is Trish McEvoy, although I'm going back to Armani again. Eyebrow pencil is IT Cosmetics. Blush is Armani. Lip pencil is Marc Jacobs. Lipstick tends to be Armani but can be Clinique, Laura Mercier or Marc Jacobs.
If you have great skin, you can get away with cheaper brands and still look fabulous. When you have problem skin like mine, looking fabulous does not come cheap and it takes a lot of effort to find the 'right' make-up.