It sounds like you're looking for a mid level laptop (closer to low-end rather than high-end) but you're shopping for a high-end laptop. Do you really need 8GB of RAM? Do you need an SSD of 256 GB? I'd say you probably need neither and would probably look at 4GB of RAM and an SSD of 128 GB.
Do you specifically want a Toshiba?
If you don't, this HP laptop is probably the same quality and some $500 cheaper after codes and rebates.
http://store.hp.com/...ontractId=10003
http://slickdeals.ne...rc=featured-377
I don't know how anybody would get by with a 128GB drive... unless they're paying fees forever for cloud storage... I always needed more than that ever since about, um... the early '90's... and that had zilch to do with entertainment media...
256GB is as small as I would go, and even that's pushing it... because even if you're not intent on building a media library, there's always somethinig you wanna put on there anyway, whether it makes sense or not.... and, while there is tons of free cloud storage available, I'm not sure I'd trust the kind you don't have to pay for... (maybe that's being paranoid, but still...)
Extra RAM is cheap... with a fast SSD it matters less, but still... I think having 8 is a good thing, especially if he might not feel comfortable adding more later if he needs it...
I agree with you about the brand issue... Toshiba laptops are one of the last-ever things I had actual brand-loyalty to... I bought nothing but them for over a decade... until my bride had 2 in a row that had fatal issues about 10 minutes after the credit-card-doubled warranty ended... (this was about the same time that Michelin priced themselves out of me having brand loyalty to their tires... so the last two companies I had brand loyalty to arranged for me to get over it at about the same time...)
It's not that I wouldn't buy Toshiba these days, it's just that their name no longer means I would... and I fully agree HP can be had with great pricing if your time frame permits you to watch the pricing and coupons for a month or so...