Your first scenario could very well be legal under Part 91, depending on the lease arrangements.
Having a 135 client that wants to go on a trip at the same time on multiple days does not constitute a "scheduled" operation by FAA definition. As B2N2 mentioned, that is more like an airline schedule, where the 135 company has a "Flight 1273" departing 0730 every day, or such. Duty times, I can't tell from your description exactly what the situation is, but yes, in general, a rest period must be 10 consecutive hours, and that means free from any duty requirements, not on call, not required to answer a pager or company phone call, etc. There is no required standard for rest location, so theoretically, the company could leave you in the crew lounge, or on a cot in the back of the hangar, or even with a sleeping bag on the floor of the plane, as long as it meets the 10 hours. A good company, though, would provide a day-room at a hotel or a crew apartment for the rest period. So, for a client that wanted a long day away, let's say you start the day at 0700, and arrive at destination and are off duty at 0900. To stay within one duty day, you would have to be "back home" and done flying by 2100. However, if you stay there, completely off duty, for 10 hours (or more) your new duty day could start at 1900, to take the client home, but not before, with the new duty day going up to 14 hours, or all the way till 0900 the following morning.
Many of the small freight feeders (FedEx caravan or UPS contractors) run on a schedule like this, the pilot rest period is accomplished all day at the "out-station," rather than at night where the flight originates.
That scenario must also be arranged prior to going off duty. It does not meet the legal standard for rest to be pacing around the FBO crew lounge all day thinking the client may show up for departure after, say, 8 hours on the ground, but they stay longer, and show up, for example, after 11 hours.
Last edited by 340drvr; 16th Jun 2017 at 11:43.