How do I Drive High Side MOSFET in High Voltage Low Power DC-AC Unipolar Converter?
So I found a solution that is not only super simple, but works extremely well.  All that is required is a resistor connected between the gate and source of the high side transistor, and a DC blocking capacitor connected between the MCU output and the transistor gate.
The resistor makes sure that Vgs = 0 when the transistor is supposed to be off, and makes Vg track Vs so Vgs is never violated.  When the MCU output is low, the capacitor is charged to Vo.  When the output is toggled high, one side of the capacitor is at 5V and the other is now at Vo + 5v.  While the transistor is on, the capacitor discharges through the resistor, and Vgs decreases slightly.  As long as the duty cycle is kept short (and RC long), Vgs(th) will always be satisfied for the entire high pulse.