I have read your other thread.
The main problem you’ll encounter is the processing speed of your brain.
Most people when they walk in the door have a processing speed of 65-70mph. Not joking......it’s the speed limit.
They can process information and make decisions relatively well as they themselves are moving at that speed and so is other traffic.
Why do people start driving slower as they get older? Their processing speed slows down and they can’t deal with situations and information that quickly anymore.
Below 10,000 everybody flies the same maximum mandated speed which is 250kts aka about 300mph.
You can’t really put a 2 year time frame on your plan if your brain is not ready for that speed yet.
Initially in a light single you’ll work at 120kts which is the cruise speed of pretty much anything with 160-180hp.
Cirrus it’s up to 180kts, same as light twins.
A single engine turbine will get you in the same speed range as a VLJ below 10,000.
Unless you’ve had a heart attack nobody dies in cruise flight.
Most trouble is in the first 18,000 and the last 18,000 feet of your flight and things go into critical stage below 10,000.
This is the Terminal Area and I mean that just as ominous as it sounds as this is where people make mistakes that will kill them. Departure procedures, arrival procedures, instrument approaches, terrain clearance, situational awareness and a big killer...weather.
Enroute in cruise you can avoid weather but you can’t in the Departure or Arrival phase, you’ll have to deal with it. All while you’re moving at 250kts/300mph.
This is the biggest problem with ( with all respect) non-professional pilots moving up into professional airplanes too quickly. Their processing speed is not commensurate with the equipment they’re flying .
The flightschool i was working at had at some point in time plans to put a Diamond Jet single engine VLJ on the line and we were planning/discussing stages of training programs to get somebody from walk-in to owner.
Then 2008 hit and the bottom fell out of the VLJ market.
You seem to have one problem less then most people, you have the funds.
But money can’t buy you two things: common sense and experience.
You can’t buy experience you’ll have to earn it.
My recommendation is to train in “glass cockpit” from Day 1. Do your Instrument rating right after your PPL under Part 141 in the same airplane type you did your Private in.
Do a significant portion of your instrument training at night. Then take a couple months off from training and go timebuild flying under IFR rules.
Be extremely cautious with flying IMC.
That’s no place to be for somebody with no experience.
Build that up very slowly. Overcast day at 7000’? File at 8000’ ( with no icing).
As your experience increases overcast at 6000’? Fly at 7000’ and so on.
Don’t joke around with IMC. It kills everyday.
I’ll get off my soap box.
What I stated about PPL still applies though, it’s the fun stage of flight training and should be approached as such. Doesn’t meant the training isn’t taken seriously.