Upload & Sell: Off
It would help greatly if we knew what subjects your brother likes to shoot, indoor, outdoor, etc.
Your brother is use to some pretty fast, low light capable glass, most zooms under a grand are not fast with the exception of the 17-55 f2.8 IS.
The 17-55 2.8 is fast and sharp, it's like a 28-88mm on a full frame camera, new with a hood (which is highly recommended) and a UV filter for protection, your cost is around $1200. You might look in the Buy&Sell forum for a used one, I've purchased several used items from FMers and everything has been in great condition!
If you want to stick with fast primes, for less than $1K, you could get an EF 28 f1.8 and a 50 f1.4. All are USM lenses and like his 85mm could be used on a full frame camera if he gets serious latter on; EF-S lenses like the 17-55 can not be used of FF digital or 35mm film bodies.
The 10-22 is sharp as a tack and it's distortion is minimal, it's a killer lens, it's like a 16-35 on a full frame body, but it can't be used on a full body like his 85 1.8 can and it's not a fast, low light lens. I have the 10-22 and love mine, but as of late have been using a 17-40L and it's colors, contrast and sharpness seem better, it's an f4 lens and is not fast either.
If fast, low light, isn't an issue tho, you might also look at the EF-S 15-85 IS. It covers a large focal range, like 24-136mm on a full frame body, is a really nice single wide-to-short telephoto option it has IS and is sharp like the 17-55; it's about $900 with hood/UV filter.
Wish I had a bro that wanted to spend a grand on me, with only an 85 to shoot with, I'd love either the 17-55 or 15-85 for a zoom solution; both have IS, something I'm seriously hooked on
Hope the above ramblings help...