Just to play devil's advocate for a bit...some pluses for the Harley.
Aftermarket: You can pick out anything you want from a multitude of vendors. Try finding anything Triumph in the JP Cycles catalog, or any other catalog.
Dealer network: There's a Harley dealer in just about any average size or bigger city in this country. Triumph dealers are few and far between, so if the local one blows you might have to travel some distance to get to a good one.
Fit and finish: I'd say the fit & finish on a Harley is a bit better than our Triumphs. More chrome(if you're into that), better looking turn signals, better looking wheels(Speedmasters have mixed color wheels...grey painted front and brushed aluminum rear).
Maintenance and mileage: That Sportster gets about 50 mpg while our bikes generally are around 40-45 mpg. Belt drive is lower maintenace than chain drive, and valve adjustments aren't as frequent on the Sportster.
Now to the Speedmaster, which I've had for over 3 years now. If you want a unique bike you won't see very often, buy a Triumph. It has dual disc brakes up front, which is an option that'll cost you some bucks on a Sportster Custom. It has carbs instead of EFI, so it's much cheaper to put a stage 1 or 2 setup on. If a fatter tire is something you like, a Speedmaster comes with a 170, the Sportster has 150.
The bottom line is a Triumph is about being different....being a lone wolf in a herd of sheep. If you're into HOG Chapter group gatherings, or being just like a million other owners, Harleys are for you. Triumph has a marketing slogan that says "Go your own way". That pretty much sums up owning a Triumph. It's a great bike that'll take you anywhere. I have almost 42,000 miles on my 2003 Speedmaster that I bought new back in June of 03. If I had to do it all over again, I'd still buy my Triumph. It's been a great ride.
