I can?t give an experienced answer to question number two, but your first question reminds me of the same issue I had when using large connectors on small wire. I used two solutions:
1) Strip an inch to an inch and a half of insulation off the wire and fold the wire back and forth several times to get the correct length. This retains all the copper and when soldered into the connector takes up most if the space you are now filling with solder. The wire gauge and connector size will determine how many folds you need.
2) Wrap some solid copper wire (I use 20 ga.) around the stripped end of the wire until you obtain the diameter you need to reduce the gap.
Both methods require a hot iron and patience, but they solve the gap problem.
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