I test rode an Indian Chief Vintage a couple months ago. Before I give my impressions, let me say that I'm a retired CPA, been riding since 1970, and feel that the C14 is the absolute best bike ever...at lest for me.
My take on the Indian: beautiful paint and trim, very heavy, very loud, mediocre power, brakes and suspension (due to mass?)... And very expensive. It was a beautiful bike to look at, but I could not EVER see myself picking the Indian to ride anywhere, as long as I had a C14 to ride. But it sure was pretty! YMMV of course. There's no denying the popularity of the American V-twin motorcycles, but They're not for me.
I also test rode a Diavel. Very fun bike! That's a V-twin I could enjoy, if I could get past the sticker shock. Don't see how you could ride 2 up on it, but I guess it might be possible. I have no clue as to reliability or maintenance costs.
After looking around, I still keep coming back to the same conclusion that the C14 is my favorite, (along with a KLR).