I asked around 2011 when I was considering my upgrade options. The answer by the two aviation (AOPA) attorneys I contacted was no. You cannot "lease the plane" to other legal entities from an FAA perspective.
There were two work arounds that the attorneys said would work from the FAA perspective. One is in a grey area for the IRS and there have been some changes around these rules since 2011; so make sure to talk to an actual expert, not some bloke on the internet.
First, create an LLC. Put the plane in it, and you personally put in every penny needed to run the plane. The plane LLC runs at a loss, which is tax deductible under some circumstances if used to check on your investments. There were annual caps, and also caps on number of years you can have a loss. Further, you need to be able to justify and differentiate between what you do as an owner for these companies versus what you do as an office/employee of these companies. The CPA and tax attorney, both said at the time that one little slipup in my documentation and the IRS would disallow everything. I decided it was not worth the risk.
Second, what someone else said. Establish a reimbursement rate that you must pay all employees. I have justified a higher rate above the GSA rate; but it is hard. I used a higher rate across the company before by digging into the GSA formula and changing the car value assumption. At the time, GSA assumed an older mid-size sedan, I redid it using a newer luxury SUV. But I had to pay that rate to all employees. We did it one year, and found the juice was not worth the squeeze to justify more than the GSA rate.
Among other reasons, at the time this is why I stayed in the certified world.
Tim
