Hmm, this all sounds a bit troll-ish (or perhaps just fantasy), but hey I’ll bite since I’ve got flying on the brain and not enough time to do anything productive before we need to leave for dinner.
First, get your medical stuff sorted out. Talk to an experienced AME about your past, and get that all squared away BEFORE you start filling out MedXPress forms. Bruce Chien posts here a lot and is going to become your best friend soon. The whole “I can just stop taking some meds” comment makes me think you might be one of the “lifestyle SSRI/Xanax/Adderall” types (we have a lot of them out here in Seattle). The problem is that your psychiatrist (or, insanely, primary care doc) needed to make up some kind of diagnosis in order to get insurance to pay for those drugs. So sure it might all be BS, but it’s in your history, and people who ACTUALLY have those conditions are often unfit to fly airplanes. You’ll need to convince the FAA that it’s not a big deal. That’ll take some time (and cash). BasicMed requires an initial medical, and you’ll need an ongoing one anyway since you want to fly the big stuff up high.
Second, 172s and the like aren’t used as trainers just because they’re inexpensive; they’re actually the best type of aircraft to learn in. Low wing loading, tough, pretty simple, benign handling, etc. Financially, you’re way better off just renting these. Training in a jet (or even an SETP) doesn’t make any sense. Even setting aside cost, it’ll just be inefficient and pointlessly challenging. It’d be like learning how to drive stick in a Ferrari; you’re just tearing up a beautiful machine that isn’t meant for that.
Third, once you have the minimum ratings you need to fly a jet (just MEL and IA), I think you should just go get the jet. I’m not sure you really need to bother with this step-up stuff. Get a good mentor pilot to fly with you for several hundred hours. You’ll spend a lot of money getting a TBM and then a King Air and then a Mustang. If you can afford it, just get the Mustang and hire a full-time pilot to fly around with you. Insurance is going to want to see massive time-in-type for anyone with low total time.
Speaking of insurance, insurance requirements are going to be much more stringent than the FAA’s. Which is totally fine, and you can work inside of that. Get a good mentor pilot, get typed in the jet, start logging hundreds of hours of PIC time together with that mentor, and then whenever insurance sees enough hours to cut you loose, you’re set. Do real trips with that mentor pilot. Fly long distances, fly in weather, fly in low visibility, fly in some icing, make a trip to KASE and fly the missed there, do some 2AM departures and arrivals. Use the airplane like the transportation machine it is while you’re training, and you’ll be a more skilled pilot than the thousand-hour CFI who zooms around the pattern all day in a Seminole in Arizona.
Now one big caveat: you probably don’t know exactly what you want now. It’s easy when you’re coming into this world with no experience to pick pretty much the most capable aircraft on paper that you can afford (more on that below) and say: “BINGO: THAT ONE.” But there are a lot of missions where something like a TBM or a King Air (or even a piston) are actually better suited. Take short field performance, for example, where most jets struggle. How long is the runway at the airport closest to your home? Are the hangars big enough for the wingspan of your bird? Would you trade 50 knots to have a fifteen minute commute to the airport instead of 90 minutes to the bigger field? Turbines aren’t great for short trips, because you need to climb them every time. Some of the really fast planes have terrible range, and if your trips are longer, you might do quite a bit better in what seems like a “lesser” aircraft. A B200 is going to beat a Mustang on a 1,700nm trip, because the King Air driver doesn’t need to stop to tank up. My point is that there are a ton of variables here that you probably haven’t had a chance to think through yet.
You’ll learn a lot of this stuff as you progress through ratings, so don’t get your heart set on too much airplane too soon.
Now, on the money front, be sure you really understand what you’re getting into. The initial acquisition cost is basically a down payment. With a jet (but any airplane, really) the true cost comes later. An overhaul of a turbofan engine is about a quarter-million dollars, and you’ll have two of them. I think you’re probably going to be at about $3,000/hr not including your mentor pilot. So assuming you fly 100hrs/year, you’ll have purchased the entire airplane again after ten years. I’m not saying you can’t afford this, but writing the check to the dealer is just the beginning. If you got a $10mm settlement from MS, don’t plan to work again, and think you can afford sole ownership of a jet, I think you’re making a terrible economic choice here.
A few pieces of misinformation seemed to sneak into the thread: you don’t need a commercial cert or a first class medical or anything like that. A third class medical and a private are all you need if you’re not doing this to make money. Your type rating will be to “ATP standards,” but you don’t need an ATP (nor will you get issued one without the requisite experience).