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I am low time PP and my boss is considering getting a license to use for commuting to various real estate investments we manage around the North East. He has been asking me for a while to fly him to one of the sites but I have always declined because of the prorata share rule I would not be able to be reimbursed for the flight and also because I am not comfortable with all of the airspace that would be involved. He has now said that he would like to go for the flight with a CFI on board so he can get a taste of the what the trip would be like using GA to help him decide if he should get the license. I would like to figure some way for him to pay for the flight and sit in the back while I get the PIC time in a safe a legal fashion. Here are my questions.

1. If we brought a CFI along for the trip (300 NM with stops in 2 cities), it would probably be a full day, how do you suppose he/she would charge for time?

2. If I flew the flight from the left seat with the CFI in the right seat could I log the time as PIC/Dual and could my boss pay for 100% of the "lesson".

3. Does this concept make sense?

4. In general can an employer reimburse a PP for expenses from a flight to business destination the way they would for a similar drive?

Thanks in Advance,

AJS