ahhh the insurance company thing... that ol chestnut...
To be honest I think this is a bit of an old myth as I personally have never been held back because of the insurance company, in my career and I have flown some aircraft without the so called requirements that everyone has in their head. 500 multi 1500TT ect.... maybe I have been lucky.
My understanding is that experience set out in company policies can decrease the policy amount and decrease the excess required to pay. However items like simulator training do not (go figure, as they do in the USA).
The idea that the insurance company will not cover a pilot is stupid as how many owner flyers out there have machines way above their experience levels... the closest I know of was an owner of a single pilot jet required to have 50 hours Icus on the aircraft before PIC and he only had 600 hours.
But yes.... times are changing