I prefer the Barons/Bonanzas. But the Lance/Saratoga have the best interior deminsions by far. Lances can be compelling bargains for little money and 13gph.
A new G36 or SR22 is the same price as a used Citation or KA90. He needs to move 5 pax plus bags. That's NOT piston territory. Get rid of the instructor, buy an SR22 and call it.
I buy JetA for $3 per gallon or less. My Pilatus is 100 knots faster than my Bonanza. My G36 always had $30K annuals. Pilatus has never had one over $11K. I'm on the fence whether the PC12 is costing me more per hour than my G36 was. Granted, a Citation or KA will have much higher OPEX and my suggestion may be out to lunch. The OP didn't set a budget. But 5 plus bags in a piston single is "out to lunch" also.
Those are reasonable issues. On the other hand, you have to think through your mission. If you want to carry four plus an instructor, well, that's pretty hard to do in most singles, over any distance. Pressurization and altitude capability can make things much more comfortable (see the Piper Mirage suggestion above), but again increase the costs, both of operation and acquisition. How much discomfort are you and your family willing to put up with? I think that's the real question.
$30k annuals on a G36? Ouch! The Turbo Commander doesn't have $30k annuals, unless there is a five year item due (like gear or prop overhaul). And even then it's usually less than that.
Yup. That's what happens when you get integrated avionics and have your plane serviced at the Beech dealer that's going bankrupt. 2 top overhauls. Always needing new batteries for the G1000. They really got me. It was a good plane though. Never failed me.
If you are newly licensed even the Saratoga will be expensive and hard to insure. My Dad although in the 80's, bought a beech sundowner to build time. Even with 2 years and lots of hours, he needed to hire a pilot for the first year in the Saratoga to get insurance. Id get the flight time in the Saratoga and then move up to a twin or turbine single. Friend has a Mirage and believe Piper has the lousiest build quality in the business. Id go used TBM-700 ten times nicer and better performance.