Can you find an old copy of Excel from before MS Office got the ribbon and went all XML and added the x on the end of all the document extensions? If so, I'll post the font editor spreadsheet I wrote. You could try it on the newer Excel, but I suspect it uses stuff that's been depreciated.
Your transistor idea is making a little progress but is still defective. Apart from not showing the +HT feed to all the MOSFET sources (pin 2), it has major issues with the bipolar transistor drivers.
You are using P channel MOSFETs to drive each segment anode, but you need to pull their gates low to turn them on, and NPN emitter followers can only drive upwards to a maximum of one diode drop below their base voltage. If you attempt to pull the bases down while the gates are charged to +HT, you'll Zener the b-e junction which does culminative damage to most types of transistor degrading the H
FE.
If you add pulldown resistors on each gate to turn on the MOSFETs, the NPN transistors could drive the gates up, but the base voltage would need to be the same as the MOSFET source voltage to actually turn them off which means you'd need a level shifter between the transistors and your [IO1] control signal.
Also the segment control signals [A]-[F] wont work the way you hope. If they are above Vb [IO1], the transistor will draw current from them to feed the emitter, but if they are open circuit the emitter will still reach nearly the same voltage, but all the current it needs will flow through the base. If any of them are below [IO1] by more than approx 0.6V, they will draw an uncontrolled amount of current through the forward biassed b-c junction and pull down [IO1] with a risk of damaging the chip driving it.
Furthermore, even if you could resolve that issue, so that the transistors successfully combine [IO1] and [A]-[F], you'd need to make sure that the level on [IO1] to activate the Grid MOSFET: LOW is the same as the level needed on the transistor bases to turn the segment MOSFETs on, otherwise it wouldn't gate the segments for a particular digit through to the multiplexed display the way you are hoping.
Doing logic with 'bare' transistors is difficult - that's why historically there was a push to integration leading to ICs and the 7400 series logic families, rather than simply using transistor arrays with all b, c and e pins prought out individually like
CA3096. To try to do level shifting from 5V TTL or 15V 4000 series CMOS up to 25v-30V for the VFD in the same device at the same time makes it even trickier. You are certainly going to need a mess of resistor and probably diodes to make anything workable. Imagine a two 'digit' two 'segment' per 'digit' VFD (i.e. two grids and two anodes) and try to figure out how to drive that with just discretes. If you can design a circuit that will generate the correct signals to drive that, extending it for 7, 14 or 16 segments and more digits is trivial.