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Yes, you should tin and wires before attempting to solder them to something else. When tinning I tend to lay the soldering iron down on the bench, place the end of wire to be tinned on the tip and then apply the solder to the wire, not the tip.
The reason you should use the solder on the wire rather than on the tip is to make sure that the whole join has reached a high enough temperature to bond properly.
If you only heat the solder, the wire may still be too cool and the joint may be faulty.
You can buy all sorts of clips and stands and stuff to assist when you don't have enough hands, but I don't have any of those, I just manage to juggle it all somehow.
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