Well, the first thing to look at would be your amp. Mic'ing it will only reproduce the sound coming out of it through the PA. I'm guessing you have a Line 6 product, or similar (solid state). They're known for having very thin tone.
Bottom line here is $$$
On q#2, it wouldn't be difficult at all, if you've got the chops.
Bottom line here is 'Talent' combined with 'Discipline'.
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