Single Pilot
Many years ago I flew the Citation V single pilot for a private owner with business interests all over the US. He played a lot of golf with 2 of his friends so I was usually included to make a foursome. Got to play some amazing courses. My wife was invited on any trip that there was room, all expenses paid. His theory was "he kept me away from home enough on some trips so it was only fair that he repay her for my time away". We flew about 200 hours a year but quite a lot of overnights. Pay was above average (as it should have been because of only one pilot) and the benefits were great. Stayed in the same resorts as he did (if we wanted to) had dinner with him and his wife (if we wanted to). It was a great job, I would still be there had he not cut back on his schedule and put the aircraft up for sale.
As far as flying the plane single pilot, that was easy. The BE200 we had before that was more complicated and we flew that single pilot. If you had a problem, let the AP fly the aircraft while you run the checklist. If the AP failed the V was so easy to trim and hand fly that it was a nonissue. High density areas (ie the NE) with inclement weather would warrant putting a freelancer in the right seat for an extra set of eyes.
If you have any questions PM me and I will answer what I can. Like I said that was quite a few years ago.
BYW, 501 driver, we did operate in the Caribbean single pilot.