The problem is that he has taken free advice from the IoD and therefore (as I have pointed out to him) he can't sue anyone if the advice is wrong.
I have a rudimentary tax knowledge and I think the advice he has been given is wrong.
The basic facts - there is the PPR and a second home (currently a holiday let, but clearly the rules are changing and it will be liable to full CGT).
He has been told that he can sell his PPR, pay no CGT on it, then move into his second home, designate that as his PPR and then pay no CGT when that is ultimately sold. Or if he lived in it until he died it would only be subject to IHT.
That doesn't seem right to me. I can't believe it's that easy to avoid paying tax on a second home.