Basically, it sounds like you just got your learner's permit to fly a small personal non-commercial plane, and instead, you went out and bought a fighter jet... 

He's a fake billionaire influencer: "look at my car, look at my boat, look at my plane now send me all of your money so you can be like me" type of guy.

Financing the purchase and maintenance for a plane is a far trickier and riskier feat than flying it.

When people reach out to me about investing out there the first thing I ask is when are you planing on flying out there for the first time.

I would definitely get on a plane and visit.

Would prefer to do something closer to home so I can avoid having to get on a plane to monitor the deal. 

You can teach yourself to fly a plane, but someone who has done it 1000 times and has a team behind them is going to be better at it. 

And if you do end up doing it, you better get on a plane and spend some real time in Ohio.

@Kumar R. of course you would never get on a plane and fly to Galveston for a vacation; that's not the point that is being argued. 

This will put you into your 50s.If you feel it will be a slow transition and you plane to concurrently carry your current source of income, that will eliminate you free time and add stress to the family dynamics and your health.In the next several years, the most crucial child development years in my opinion, you will not be there for your kids ...