Should he get comprehensive insurance for his car so that the company will compensate him by as much as he paid?

Praise be to Allah.

Firstly:

Commercial insurance on cars and possessions is haraam because it is based on usury and gambling, as we have explained previously in the answer to question no. 8889.

Secondly:

If someone is forced to take out commercial insurance, it is permissible for him to do so, but he should limit it to the minimum option, and not overstep that mark, because what is necessary should be estimated properly, without overestimating. So he should take out third-party insurance on the car, not comprehensive insurance.

Shaykh Yoosuf ash-Shubayli (may Allah preserve him) said:

If the law in the country where a person lives makes it compulsory to have insurance on cars, otherwise he will be regarded as breaking the law, then it is permissible to take out insurance in this case, because there is a need that dictates doing so.

But he should understand that if the law obliges third-party insurance only, or a lower option than that, then it is not permissible to do more than that, because anything more than that is not dictated by necessity. One of the established principles in Islamic law is that what is necessary should be estimated properly, without overestimating. End quote.

Thirdly:

It is not permissible for you to insure your house if you are not compelled to do so, and it is not permissible for you to take out comprehensive insurance in order to be compensated for the amount that you have paid, because riba is not permissible except in the case of necessity, and there is no necessity in this case.

And Allah knows best.