Hey Kev.
My 04 America (Sophie) has only had one issue - a troublesome oil pressure switch that was replaced under warranty. Other than the regular services the only surprising thing has been the relativley short duration of the rear brake pads (about 9000km/5000miles). Having said that, replacing them with sintered metal pads seems to have solved that issue.
Of all the bikes I've read about on this site I've only heard of two "lemons" which is a pretty good average. Another benefit of the Triumph over the Honda (other than character & street cred) is that the european bikes hold their value better than the japanese ones.
I've done 23500km (just over 14600 miles) in 18 months and she's never missed a beat. As for needing a bigger bike, I tow a trailer with mine regularly and have done so with a pillion, so you shouldn't have too many worries there.
Matt
