As per above, four years is a little longer than I would try to get out of a laptop, at least as my main computer.
I would start with what he is going to use it for. Is he going to play games on it and want the power of a discrete GPU or will he be fine with integrated graphic? If all he is going to do on it is browse the internet, create and edit documents, and maybe watch a movie or two, then all he needs is integrated graphics.
Next I would consider size, and this comes down to how much he will be lugging the machine around. A heavy laptop with a large screen can be cumbersome to carry around all day. Both of the laptops I have for college are around 14in, and I find this easy enough to carry around. If he is going to be watching movies or playing games, he may want a bigger screen.
I wouldn't go lower than 320GB for a single drive machine. Movies and music are just to big to go smaller and even Windows can start to take up a lot of space after a while, and, while he should have an external hard drive for backups, I find externals to be very easily lost and stolen when one carries them around. I would probably look for 500GB. As for RAM, the minimum I would consider is 4GB, preferably 8GB.
I use Windows 8 on two machines and I have a strong dislike of every aspect of its user interface. On a laptop (without a touchscreen), it is slow awkward, and fragmented in it use. Gestures needed to do do basic things, like switching to another application, are difficult to do on a touchpad. Full screen apps are a joke and hurt parallel productivity, and splitting the screen between two apps helps very little. I use it because it's fast and I tolerate it because I was willing to spend $15 on software to fix its (glaring) problems. With a touch screen, it's a whole other story. Windows 8 actually makes sense, the awkwardness replaced by fluid touch gestures.
Practically speaking, I would get a Windows 7 machine, if available, unless I wanted a touchscreen.
As for brands, I like Asus, Lenovo, MSI (high-end), Samsung, and certain Acer machines. I dislike Fujitsu, Dell, Gateway, and Toshiba.
I haven't used a HP machine recently enough to judge them. My opinion on this matter is based solely on my own experiences, and some may have different opinions based on their own experiences. As for Apple, they build great (if overpriced) hardware and their software is clean and user friendly. However, I dislike the 'iCult' that surrounds their products, and the controlling nature of their devices.