A co-worker of mine bought a new 2006 Sportster 883 about 2 weeks before I bought my Speedmaster. Overall I think he's very happy with it, but it didn't take him long before he starting saying he wished he bought a "bigger" bike - not necessarly bigger in power, just bigger physically. He jokingly refers to his bike as a "sissy" bike - he recently put new pipes on it so at least it won't "sound wimpy." His words, not mine.
I haven't ridden the Sportster but it seems like a nice enough bike. One of the main complaints from my co-worker is that he doesn't feel it's very comfortable for long-rides and it apparently has a smallish fuel tank, so he has to stop more frequently for fuel on longer rides.
The first day I showed up with the Speedmaster we took a ride to lunch. The look on his face when he first saw it pretty much said it all. He wasn't familiar with the Triumph line before, but I think he was really interested after he saw mine.
Tell your brother to ride them all and pick the one he likes best.
