There's a good chance that I'm going to end up with one of these in my garage.
I'm working on getting my girlfriend into riding and since she's only ever been a pillion (and only giving riding her own bike shot because of my urging) all she has to go on when choosing a bike is comfort and style.
I know style is utterly irrelevant for a first bike. In all likely hood she'll outgrow her first bike in a year or two. However to her style is very important. So I've been researching good starter bikes and showing her pictures to see what she likes. I'm hoping that by getting her a bike she's attached to, she'll be more enthusiastic about riding and through practice learn what makes for a good (to her) bike.
So far she doesn't like anything that looks 'modern'. She doesn't like the newer Kawasaki Vulcan, any sport bikes, naked, street fighters or ADVs. She is ambivalent to the smaller Honda, Yamaha and Suzuki cruisers. She does like the Streets and the 883s and she also likes Bonneville and the Scrambler Ducs. For some reason I haven't found a Superlow that she has liked.
I took her to the bike shop the other day so she could throw a leg over a few models. I had her try Yamaha and Honda 250s as well as the Scrambler Duc and an 883. She's all of 5ft 2in and, uh, lets say 'stocky' so I was a bit surprised about her feedback. The Scrambler was too tall, naturally, it would probably work with the narrow seat and an aftermarket lowering linkage I've seen, but she wasn't terribly comfortable on it. She said the 250s felt too small and frail which was the big surprise. I thought she'd be more inclined to one of those. The only bike she was comfortable on was the 883.
Now having spent a great deal of time researching starter bikes I know the 883 and the Street have similar ergo profile and by all the reviews I've read the Street is a better handling bike. So when she gets her endorsement and it's time to get her ride, I'm going to take her to the HD dealer and have her try on the Street. If she likes that bike more, that's what we'll get. If she does choose the Street, we'll be buying new since the first run had some major brake issues, a recall for the fuel pump and some issues with the hardware quality that appears to have been addressed in the 2016s. (though I'm honestly hoping she prefers the 883, I can buy a used one of those for cheap!)
If we do end up with the Street, I'm just going to chalk it up as an investment into getting her to ride.
@Rocket Scientist I think the cafe racer cowling does a lot to improve the look of the Street.