THE AIRCRAFT HAD PREVIOUSLY BEEN FLOWN FROM ORLANDO, FL TO NORFOLK/CHESAPEAKE, VA. WHILE THE ORIGINAL NON-INSTRUMENT RATED PILOT WAS IN VIRGINIA, THE WEATHER DETERIORATED, SO THE OWNER FLEW UP FROM ORLANDO (VIA THE AIRLINES) TO FLY THE ORIGINAL OCCUPANTS BACK TO FLORIDA. A WITNESS REPORTED THAT BEFORE TAKEOFF, THERE WAS A DISCUSSION ABOUT HOW THE NON-INSTRUMENT RATED PILOT COULD GET SOME INSTRUMENT FLIGHT TIME ON THE RETURN FLIGHT. FOR THE RETURN FLIGHT, THE OWNER OCCUPIED THE RIGHT FRONT SEAT AS THE PILOT-IN-COMMAND. HE STATED THAT DURING TAKEOFF, THE NON-INSTRUMENT RATED PILOT WAS FLYING THE AIRCRAFT FROM THE LEFT FRONT SEAT. THE OWNER STATED THAT HE REMEMBERED THE OTHER PILOT REACHING FOR THE LANDING GEAR HANDLE TO RAISE THE GEAR, AND SECONDS LATER, THE AIRCRAFT HIT A TREE. ONE WITNESS REPORTED THAT HE COULD SEE THE AIRCRAFT AT ALL TIMES DURING TAKEOFF FROM LIFT-OFF UNTIL IT CRASHED.