Haha yes, that was a building of text ^^ I'm pretty new to multi-boxing myself but I will give a go at some of your questions.

1. Thats a tricky one, that could go either way. But I'm gunna say I think you would be at risk. Not 100% though.

2. If question 1 isn't a problem then as far as I know he is fine to play the shaman, because blizz doesn't check into it, unless you get reported. In which case you would not both get reported, so when checked by blizz you would both have all your chars on accounts with the same names.

3. Yes, as I said in 2, I don't think it would danger him to play the shaman you started, so him starting a new char should be fine.

4. If I were you I would use the 5th account, I think its safe.

I hope that helped somewhat, sorry I'm not 100% on any of the questions inch:
oup?