In ALL cases like this, you really do need competent, experienced, legal counsel to make sure that you don't unintentionally violate any regulations. There are many "gotchas". 18 months ago we were in the middle of doing something similar. We ended up using an attorney and it really kept us from getting in over our heads. As we discussed our particular situation I mentioned 91.501 and a few other regulations. The attorney countered with FAA interpretations and court rulings that really altered what we were able to do and how we were able to do it.
The bottom line is that when it comes to legal matters and bureaucracies, things are never simple. This especially applies to the FAA. The problem is that the FAA doesn't have the manpower to police every little aspect of our operations. (Thank goodness!) Many legal issues don't come to light until, as Bluefishbeagle said, you have an accident (or an incident, or a ramp check...) Then it's too late and the legal and enforcement fun begins. (Let's not for get the possible insurance ramifications as well.) Some people think that because they been doing it a certain way for years that it's OK. Not necessarily so.
In our case, I resisted following the attorney's advice at first - this issue seemed so cut and dried and couldn't really be that complicated and he was making such a big deal out of it. He finally convinced me and was able to come up with a program that allowed us to do exactly what we wanted to do. It is significantly different from the way I had contemplated doing it using the "conventional widsom" that I have accumulated over a 41 year flying career. The cost was minimal and I can sleep well at night knowing that ALL of my "I's" are dotted and my "T's" are crossed.
LS
Note: Results not typical, your mileage may vary. Offer not valid in the states of Minnesota, Louisianna, and New York. No animals were harmed in the posting of this thread. Hillary is insane.