The 'charter' business was flourishing when I was learning to fly 55 years ago. I know of three fatal accidents involving such trips, one fortunately on his way to pick up his passengers (hence his need to fly into IMC containing a very large rock) another in which the pilot was killed but passenger escaped with serious injuries and the third in which both persons died on a photographic trip which went 'just a bit lower and slower' for a better picture.
I agree with Hot'n'High that insurance may be the key. People need to be told that life insurance policies associated with mortgages, businesses etc. do not cover private flights, the normal requirement being a multi-engined aircraft flown by a commercial pilot under an AOC. If you get killed, and Wingly and the like carry a greater risk, then your family will be left penniless. One such case has already been highlighted in this thread. It is possible to obtain this cover, as I did in our flying days, but the premium loading will be substantial to reflect the extra risk.