I'm a new guy embarking on flight training myself. Keep that in mind as it means my opinion is probably worth squat.

If I had the money it sounds like you have (God bless the Cali. housing market, eh) I would buy an airplane since the resale price is always pretty good. Get yourself something like a multi-engine IFR, one that you can put the family in. Hire a flight instructor and get your private. Once you have the private, take the family EVERYWHERE. Log hours like crazy by taking vacations and seeing every state, etc. Put the kids (if you have any) in a year-round school and then every time they are on track break go fly somewhere. Take the wife to dinner in the next state. Fly yourself to the home team's away games.

If you're willing to move, might as well move to a city that has great schools for the kids so they can get a good education. Any city with a small airport will have flight instruction so you can move just about anywhere. Pick a city that will be good for raising a family.

Then, when you finally get hired at your dream job, you can sell your plane if you want and get a selling price that is just about what you bought it for.

If I had the money, that's what I would do. Since I don't I will stick to eeking it out.