Giorgio Armarni Luminous Silk is probably one of the best for that sort of look. It’s not the most coverage-y foundation out there, but it’s definitely enough to even out your skin and cover minor imperfections. It looks really natural and glowy with or without finishing powder :)
I’d usually say go for quality pieces that’ll last but in this case you don’t want to spend too much and you’d need a fair bit to be able to play around with different outfits each day, so just go for places like Asos & Romwe - don’t worry if the clothes will or won’t last a 1000 washes or anything, it’s just a cost effective way to dress for school/college and you won’t be worried about ruining them in any way on transport or with the constant wear and tear :)
Just had a quick look over a few sites with similar items and American Apparel is probably the best for that price definitely. There’s a few cheaper ones on F21 & such but they don’t look quite as nice :)
Contouring will be your best friend, MUFE has an amazing kit of shades just for this (as do a few other brands, but haven’t tried them). It basically just involves emphasises the high points on your face (nose, browbones, cheekbones) and shadowing in the lower points around them to create dimension. There would be a ton of youtube tutorials you could watch to get the hang of it, like this one. Good luck!
The stains should definitely come out - you can soak them in soapy water, try not to scrub them too much as it can ruin the bristles. Alternatively, MAC and a few other brands make solutions purely for cleaning brushes and some of them work wonders :)