There's several Harleys in my desired price range, but every single one of them has a history I don't like - either a lack of paperwork proving claimed work to address the cam chain tensioner issues, or low mileage engines that just have never been touched...which means they're basically ticking timebombs. The other thing that I'm seeing are bikes with endless performance hop-ups which people seem to think is a plus, but I personally consider to be a negative as it means chances are it's had a rougher than average life.
I'm still looking, but the only really ideal one I'm seeing that looks like it's properly upgraded (with paperwork to prove it), and is owned by someone who rode it as the 1000# touring bike it is (instead of trying to make it a crotch rocket by adding tuners and junk) is 5 hours away. The pictures look good, but several past really bad experiences in my past have made me once bitten twice shy about going long distances for vehicles that are promised to be in one condition online, but turned out to be enormous turds upon arrival, with the posted photos clearly being a decade or more old.
Back on the metric front, I went and looked at the Kawi Voyager today that I'd been eyeballing. It's nice. Checks all the boxes and is in good shape. Not 100% sure on the seat (even though it has a factory optioned "comfort" seat option vs the stock) but seat issues, if it even turns out to be an issue (One can never really tell until they get that first long ride under your belt), is easy to address. The one big downside is...well...it has a tune flashed on it which does create the question of whether it's been thrashed as well, but having spent some time with the owner chatting, I didn't get the impression he was the sort to beat on it. But the tune means it needs premium fuel, although some digging shows the bike requires minimum 90 octane anyways (mid grade) so I guess at that point we're only taking a few dollars per tank difference regardless.
I've got a few others to look at as well, but I suspect I'm going to keep coming back to the Kawi.