Can you be covered under two different personal umbrella insurance policies and how would they pay?

There is nothing wrong with having more than one insurance policy of any particular type, so long as you are not trying to seek double payment, which would be considered felony insurance fraud and comes with lengthy prison sentences.

The policy with the broadest scope of coverage would be considered primary or first position coverage. The secondary policy would not invoke unless the limits of the first policy as well as the underlying policy have been exhausted.