It seems to work for people that don't have a passion for sailing but not so much (in my experience) for those that do. I know, you're not doing it for a living but you'll be investing $ in the big cat and all the stuff, solely for your business model.
On the other hand, if you love the big boat still, as a couple, taking a few charters could be great fun. Especially if you drop them off after a few hours. I'd hate to think I was trapped onboard with a new found idiot, even for just a few days.
And my wife would simply jump ship and swim to shore. "I'm outa here, see ya on Tuesday, Tom"