I assume you're asking about modern Hinckley Triumphs and not the vintage Triumphs.
I very much doubt that you will find any definitive answers to your questions other than the obvious - 2020 models.
However, maybe somebody can come up with some historical data.
My favorite are the early, carbureted models. My reason is they are as reliable as it gets. Simple electronics, simple carbs. Simple no fuss, get on and go. I had my choice when I bought mine used. I went with a 2002. I liked the shape of the early tank and 7" headlamp. ...J.D.
I have a 2007 carb model Speedmaster. The bike looked new and for $1800 I couldn't beat it when I purchased it last November. It came with an airbrushed front mud guard with Marlon Brando and his Triumph in "The Wild One", plus a CD of the movie. It also had a windshield and the light bar. I added the Viking bags in the back. Not the big ones, but enough space for what I need. I added the battery tender and also wired in a triple charger so I can keep my phone etc charged. Other repairs included chain and sprockets, replacing seals in the front forks and installing the original factory mufflers on the bike. The 2 new( but on the shelf for 13 years) mufflers were $75 each, the fork seals were $28. So far I love the bike. As a kid growing up in South Africa, the ultimate riding machine was either a Norton Commando or a Triumph Bonneville.