May a commercial pilot transport an owner in the latter’s experimental aircraft for compensation?
This one seems pretty straightforward to me. 91.319(a)(2) applies (because in the scenario you have described the pilot would be carrying persons - Olive - for compensation or hire). 

Popeye could accept compensation to reposition the aircraft (with no passengers or cargo onboard) as a ferry pilot, but not to operate the aircraft for the purposes of transporting persons or property (besides the aircraft itself and the incidental things it might carry like extra oil) - even if the person happens to be the owner of the aircraft.