I personally feel that a good quality analog preamp will outperform a digital one, so I'd go with #2.
However, your speakers are a somewhat weak link in all this, so yes, you'd want to replace them in order to get closer to the "singer in the room".
I don't have experience with the speakers you mention, but in an overall sense, I'd recommend you put as much money as you can into the speakers and work backward from there, not starting with the amps and working forward to the speakers.
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