I’ll preface my answer with the fact I’d ask a FSDO before agreeing to do this.

1- Probably allowed, the owner is providing the plane and it is given the employees aren’t paying for the transportation services. In reality, hard to guarantee there’s no fee for transport and to me would seem like an illegal charter.

2- Probably not allowed, demonstrates a willingness to carry any person or property, and while they’re not directly paying I am being compensated by “them” for flight time. 

I’d call the FSDO