I've been contemplating the same things you have. You can't beat the powerband of a NA motor, and boost is definitely easier. With that being said, the aftermarket on the VQ37 motor hasn't really picked up it's full potential yet. If there were a cam and VVEL tuning available, I would definitely have gone for it, but the way things have been going it doesn't seem very likely that this will happen. You won't be able to uncork the full potential of an NA VQ37 unless someone can crack the VVEL and do the legwork on cams/shims etc.
With the TT/supercharged route it seems easy to just up the boost and be done with it. If your boost isn't substantial you can always have a reliable platform.
NA power is always harder and cheaper to obtain the same HP numbers with.
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