I don't know how I completely missed this post earlier Shannon. I can't believe you bought a leather Jacket, posted it, took it home and returned it and I missed the whole thing! This board moves very fast sometimes!
I would have been a nay. Mostly because of the neck. I also just feel like you are a little more cool than that jacket. Not that it had to be more edgy, but I almost think a piece like that where you are making such an investment and expect to be a workhorse should strongly personify one of the elements in your rubric and to me, that one looked too compromised.
I don't have a lot of investment pieces in my wardrobe but I do in other areas of my life and I think if I were going to invest in an item I would want a strong emotional reaction to it rather than something that just "works", even if by an observers eye it looked good on me. I feel if I didn't, then sure enough something would come along that I did feel giddy about and then I would be stuck with the just ok one, or else I'd buy the awesome one too and then the other would be unloved.