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I’m alright with cold to a point and rain to a point but both together (plus dark mornings/evenings) are just miserable. My mighty Punto is making itself useful at the moment.
There are quite a few HD riders at work and they mostly look and sound amazing but I reckon the open road fantasy is mostly just fantasy.
Dramatic_Hammer-
I've done 2 big tours on HD full dressers and ridden them on 5 continents :). It's probably the best way to experience them. LA and touring round the National Parks is amazing, I still want to go back and do the coast there. Surrey and the coast in the summer is nice but it's not the same thing.
Probably people get into the owners group scene and it gives you some rides to attend and social activity around buying new chrome parts. It doesn't suit me on a day to day level but it's good to have an idea of what they offer in case you need to get one in a hurry!
Airhead
It's worth getting into it early, otherwise you miss the start of summer. If you're going to be a fair weather biker, and that is better that not biking at all.
My advice about Harleys as an experience would be to get the biggest engine you can but not necessarily tuned. The whole low down torque of the big engines is most of the fun riding them. The Fat Boy with a a massive rear tyre is a nice place to be.