Interesting, my take on the Speedmaster is it's on of the most planted bikes I've ever ridden. My front tyre has a slow leak of some sort (.1 bar in a couple of days, and when it's down below 2bar it's a bit squirrely. The worst bike for having the tyres wrong on was the Guzzi V7, unless you had them about 5-10% over, the bike was quite worrying....I test rode both the Bobber and Bobber Black. I can see why Triumph introduced the BB - it has a definite presence though personally I prefer the look of the Bobber. The original is more in keeping with the minimalistic look in my eyes.
Having ridden both I can't say that I found the brakes on the BB that much better than the Bobber. To be sure if yanked really hard they had more stopping power but nowhere near as much more as I'd have expected. I'm happy with the Bobber's single disc and have reverted back to my usual two finger braking habit once I realised the brakes were better than people seem to suggest. Having said that I am not a fast rider so I'm not piling into corners flat out and then trying to slow down at the last minute.
The thing I did find with the BB was that it was much more prone to be unsettled by poor road surfaces. For example, on overtakes crossing the white lines / cats eyes / joins in the surface - the bike had a noticeable twitch. Only brief and it settled down immediately, but the Bobber doesn't do it. Either it's that heavier front wheel/tyre or the bike I was riding had dodgy tyre pressures? I've not heard others complain so it might just have been the set up on the bike I was riding.
I also found I needed to muscle it into corners more. Once turned in it stuck there fine, but the Bobber rides more intuitively in my experience - on the windy lanes around N Wales it just flows whereas I felt I was having to steer the BB into the bends.
At the end of the day I am a bit of a magpie so a shiny red and silver tank was the thing that sealed the deal.