For the short and infrequent trips I would make, it seems like contract pilots would be the way to go. One one directory, for the Lear 55 for example, there are literally pages and pages of them with their day rates posted. I'd probably build up a stable of trusted ones and use them as required. I really don't see the point of annually hiring a pilot and copilot - it would probably be a very unrewarding gig for them based upon my frequency of travel.
And it's not like I have to leave "this minute". I would gave days, even weeks of notice. My life is just not that rapidly evolving that I need to have a pilot in the cockpit keeping the engines warm.