The fathers Girlfriend is the executor

A life estate was left with the provision that she be allowed to continue living on the property and my client be allowed to continue running his business while paying all operating costs of the land, plus $2,000 monthly to her. Short version she lives there for free at my clients expense. Upon her death he receives the property from the life estate. 

Restrictions on the property is is cant be sold, or mortgaged until he or she passes. 

There were no other assets other then a tiny bank account and some small collectibles which went to the girlfriend. 

No 1041's have been filed as she is the executor and doesn't believe them necessary. 

He doesnt need permission, just more looking at if he is correct to issue it, as their relationship is toxic at best and we just want to be sure she has no recourse to say a 1099 is not applicable.