You make me feel old! My first street bike was a brand new 1979 Suzuki GS1000E my father bought for me when I was seventeen.
I have several bikes, including a 2005 Rocket and a 1998 Valkyrie. The Valkyrie is superior to the Rocket in every way, except engine power. It sounds better (with a Cobra 6 into 6 exhaust), it is more comfortable (both seating and ride), and it handles better (the low CG of the flat 6 makes a big difference). If I could only have one bike, it would be the Valkyrie.
BUT, every time I open the throttle on the Rocket I fall in love all over again. When I was younger I rode a Suzuki Hayabusa (loved it), but it could not leave the line like the Rocket does. Just twist the throttle and dump the clutch (at the same time), and it launches like a fighter jet off an aircraft carrier.
Regarding passenger comfort, my wife rode on the back of my Rocket for about 10 minutes, and will never do it again. The pillion is small and hard. So some kind of upgrade will be necessary for you.
The first year (2005) is the only year without a blacked out engine, if that makes any difference to you.
I bought my Rocket used in 2013, so I don't know about its history before that, but since I've owned it I had to replace the primary TPS (it would idle at 2000 rpm). Also the final drive unit (Triumph calls it the "bevel box"), a replacement for which I found on eBay (used). The front brake lever was soft and would pull almost to the grip, so I rebuilt the master cylinder. That's it.