Re-hairing can be EXTREMELY frustrating until you get the hang of it, after that its pretty easy. I suggest always widening the plug holes with a push pin as Kaoskat suggested, or a needle that is a little wider then your hair needle. You wont break as many needles this way.
You might also want to consider how much hair you're trying to fit into each plug and keep that in mind when you're widening your plugs before.
It can leave you pulling your own hair out, but eventually you'll get there and you'll adopt your own methods that work best for you, everyone seems to have their own tried and true ways of re-hairing. 
So just keep trying different things and good luck!
I think I was using too much hair at the start. I have found a way that works, but it's soo slow. It's just using a needle, it's going well. I've done a fair bit, but I'm having a break for now.
Thanks so much for your advice guys, you've kept me sane. ^_^
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