There are two issues here.....what you are legally allowed to do, and what the insurance require you to do.
Example, I have plenty of time in complex and turbo charged aeroplanes, and when we bough a complex TC'd aeroplane the insurance stipulated "a check out with a qualified flight instructor". This includes CRI by the way who is considered a QFI by the insurance company. This was despite legally being qualified to fly the aeroplane.
It is a good idea anyway, but in the case of a simple SEP I doubt any insurance requirement like this would exist. It would probably stipulate a minimum number of hours, and then a check out could be accomplished by a fellow group member. When I joined a group which operated a simple SEP, this was how it was accomplished anyway.