This is an interesting question for me too. I don't have a car (and don't particularly want one), and thus my bike is both a pleasure vehicle and a daily driver for most of the year. In the winter I just suffer.
I am in this awkward middle ground where I would love something with lots of CharacterTM, but I'm constrained by a number of practicality factors:
1) Money is a pretty big ish concern for me - Maintaining an Italian bike (for example) is generally more expensive, and insurance is still high-ish for me since I only have four years under my insurance history.
2) I don't have easy access to a garage or work space - Though I can and have worked on my bikes, it's not always convenient. Lately I've been taking my bike to the shop since I also don't want to spend days fiddling with something when a shop could usually get it done for me in a day. I'd love to tinker, but I love to ride more - and having only one bike means any day of down time is a day that I have to take the bus or walk somewhere. Currently waiting for over three weeks now for parts to get valves done on my Triumph, and not riding it really really sucks. It's making me reconsider British bikes altogether.
3) Not having access to a private garage also means that I park on the street. Meaning the bike can't be too valuable or pretty or attractive to a thief. I've been lucky so far.
My KLR650 ticked most of the boxes. It was cheap, reliable, and very easy to work on myself. It allowed for some adventure riding (though I did a lot less off road than I would have liked), and the Gen 1 looks badass. That bike really fit my personality like a glove. But it was slow, and not the funnest to ride on the highway (though power isn't a huge concern for me).
Now onto my Triumph Scrambler. The bike sounds AMAZING with the Arrow 2-1. Air cooled adds some simplicity over the KLR liquid cooling. Nice oomph without threatening to kill me every time I twist my wrist. Trade off is now I'm messing about with EFI tuning, and the bike currently runs rough likely due to out of spec valves, a job which is now 3+ weeks into parts wait... I never had to wait so long on parts for the Kawasaki.
Though the Scrambler is perfect for me in my current place in life in many many ways - the inconvenience of Triumphs abysmal parts availability is a gigantic turn off. It's already cut basically a month out of my riding season. A bike with Character is downright pointless if you can't ride it.
I know people who love Harley's, and I would consider building up an Evo Sportster 1200 if I give up on Triumph, but frankly the ergos aren't quite for me (in my limited experience), and they are a little too loud for my comfort with seemingly no middle ground. The simplicity and agricultural nature of the Evo is appealing to me though. And I can't really go older than an Evo platform since I am not oozing cash...
Ultimately, I keep thinking that maybe Japan is the way to go for me. Reliability is #1, sound and feel is #2 (a close second). That said, even with countless hours of online browsing, I am having a generally hard time finding bikes that reach into my soul. Damn the Scrambler is close though...
