Heck with all the money you have these are play numbers.
You hit the nail on the head when you qualified the statement, "worth it to me". I do see your point about the ratios. With all the torque these things make we do not need meaningless gears close together. I don not care that much about the extra displacement because mine does make more power, period.
You are also correct about the money and the Indians. They are costly and not all that fast , just like the Harleys I cut my adult teeth on. In '09 i paid 22k for some bike and it went up from there. If you wanted a top of the line HD you knew you were going to pay upwards of 40k, that's the way is is. So 29k ain't the end of the world. In the end I just like the look of the bike and many people will purchase chiefly looks. I do place looks high in the list which does not seem to be as important to buyers of non American brands.