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Springer all the way. Take that bad boy and make it exactly what you want. Whay pay the extra for a new bike when you already have a great starting point.
It all depends on your budget. I tend to become attached to the vehicles that I have had for a while and say rework the springer, unless you tons of money left over for the night train. If you're going to do it, do it right.
+1 for the Springer - Night Train is a badass bike, but just black out the Springer and you'll have the best of both. I understand your point about dumping the money into it (see my Avatar that ate quite a bit of coin)....but just add up your wife's receipts from Yankee Candle (or similar store) and you'll be even