In order:
1: Who can say what emotions move people, or what they will care about in afew years. I am sure that many Taylor Swift fans (who are usually kids) will hear her stuff when they are adults and look back sentimentally on that concert and what they were doing as kids. Further, I bet they could never imagine how anyone could care about going to see Nile as a kid (which I did about 10 years ago and remember fondly)
Looking back at something sentimentally and smiling is an entirely different emotional connection. The connection isn't with the music, its with their childhood. The fact that it was a Taylor Swift concert is totally irrelevant in your example, that just so happened to be what they were doing.
Your example of the Nile gig is precisely why I think music is too personal to be measured in terms of commercial success.
2: Who knows? It's a big world. But considering the number of her fans, I'd say the odds are good that quite a few will
Realistically, this will be nothing but a TINY fraction of the people listening now. This has been proven time and time again by the thousands of, "where are they now" bands whos target market were kids of a young age.
3: How can you get on a high horse about lofty musical goals and then call into question the artistic integrity of another musician? Most of her stuff is sappy sentimental teenage crush garbage, but its not for people who don't like that stuff, and might mean a lot to her as she herself falls into her general target audience. I don't propose to know what she feels about the integrity of ger music, but I am in no more position to question that than I am to question how people can find any "art" in the wall of noise that is grindcore music (which I like)
I can call her artistic integrity into question simply because I very much doubt she has very much artistic input into it at all. I could, of course, be wrong. I still think its unlikely, not because I know her personally, but because of the nature of the end of the business shes involved with. I'm not saying her music isn't artistically valid, who the hell am I to claim one thing is valid and another thing isn't? I'm merely stating that I have doubts about how involved she actually is in the creation of her art.
4: Well there ya go, YOUR musical goals. And if your musical goals involve people connecting with your music, how do you plan on measuring your success at it?
I don't plan on measuring it. Why do I
have to quantify it? I'll keep on playing what I enjoy, if its "successful", so be it, if not, I'm still enjoying it. I don't really feel the need to label or quantify just how successful it is. If people connect with it, thats great, because I do enjoy playing music in front of people, however, if they don't, I'm still connecting with what I'm playing, and thats my main priority.
The overwhelming irony of people getting all over bluewine for stating an opinion and then turning around and trying to "prove" that some other kind of music is somehow not good enough is humorous. Just say you don't like stuff and you like other stuff. That's what I do. I get more crap for saying I don't like something than for saying that success can be measured by album sales. That's pretty funny too.
I think you misinterpreted my point, that could well be my fault, I probably wasn't very clear about it. I've no problem with Taylor Swift, I wish her all the "commercial success"

in the world! All I'm saying is, "its not for me", and that just because a band sells less than her, doesn't necessarily make them less successful, because they may have totally different goals to her.