OP,
Seriously, you need to relax. Just go fly, start working on your PPC and see where that takes you. It’s good to have a plan, but you’re going over the top, and likely step 1 of your plan won’t go as planned, so keep that in mind. You’re not going to learn a thing, if you’re focused on the last step.
I had the ultimate goal of being a Fighter Pilot and then Airline pilot. I started on the civilian track, got all of my ratings, CFI’d for years, joined the Air Force did well in training, flew F16’s, T38’s, got out and got my Airline job. All along the way, my philosophy was to do the very best at my current job. It’s like losing weight or paying off all of your debt (a la Dave Ramsey), have the end goal, but it’s a daily battle.
I’m assuming you’re well off ($30+ mil net worth) since you’re considering buying a VLJ. Why not take a hiatus and go to FlightSafety Academy? I trained there in the early 90’s, it was not quite as good as military training, but pretty dang close it terms of structure.