Is it risky?
Pay the miner 5 cents or wait days for your transaction to process.
I've sent transactions before with 0 fee and still had them there within an hour. You just have to make sure the amount you're sending is 0.01 BTC or more and that the transaction size is under 10 KB.
He's a newbie, and he won't be able to calculate tx size before sending it.
You really don't have to though. I think it's around 75 inputs + 1 output (just to be safe). So if you're always getting inputs of 1 mBTC, you should be able to send 0.075 BTC in one transaction before hitting that cap. It's of course a bit deeper than this, but you should be safe with that.
He probably has no idea as to what inputs and outputs are anyway. Also, don't forget the change, so it won't be 1 output.
True. A better idea then: Coinbase! No worrying about fees since they pay for them, :p.