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Have you considered the V 85 TT? with the Stelvio, prices on the TT should come down in the used market. I have seen some sweet deals on some,and am tempted myself. Its a well proven machine, and cheaper to accesorize, I thinkRick
Check out a v9,cheaper than v85 and by all accounts a more mellow engine.
The current V9 and V7 engines are afaik identical.The magical different one was the first generation V9 (2017-20ish).
The Bonnie and W800 may look similar, but are very different machines. The Triumph is quite modern in how it feels and rides, whereas the W800 could have been made in the 1970s and not made many headlines. It is better finished, though, and is easier to maintain than any modern Triumph.
Yes, they are different machines, agreed....I like the Triumph, well, because it's a TRIUMPH! I like that Bevel Drive (like a Ducati...) on the W800 and wonder if some after-market company will come up with a "glass port hole opening" for that Bevel Drive?
The Roamer and the Bobber really don't do it for me looks wise. I'm really more a V7 person. I will be asking for another ride of my freinds V7 Mk 3 this summer to see how that compares to the Breva. There are some bargains around. 6 gears! Wow!
You might want to consider a well cared for W650, which were limited to just 2000 and 2001. They look more traditional, and still have that sexy bevel drive…
Assuming you are talk about buying new? If so why not consider used and save a bundle? I bought a higher end adventure bike last year for the original owner. It has 18,602 miles on it, like new and every option/package available. The OP had almost $30,000 into it, I bought it for under $17,000. While he had the luxury of putting on the first 18,602 miles he also paid a $13,000+ premium to do so.
It cant be anything but a Guzzi at this stage.