I can only confidently answer Q4, as Im unsure of the rest.
You will definitely scrape through your guitar's finish and expose bare wood. Now some people dont like pickguards because they they feel they are ugly and prefer a bare top.
No reason not to, other than preference Id say.
Keep in mind that a pickgaurd doesnt protect every bit of the top where your pick will hit it. Mainly the space between the soundhole and the pickgaurd is vulnerable.
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