SkyWolf,

I'd say get your pilot's certificate by paying CASH and do it as a hobby for now. And if you want to go pro later, you have the option to. Warning: You do not want to have debt as a result of flight training. It is life crippling.

You seem to be a smart guy. Do the math. Go to Airline Pilot Central - HOME and look at the regional airlines' FO pay. Open up Excel and do a cost analysis on how much you will take in, and how much you need to pay out, each month. Keep in mind that there may be days where you might have to shell out $40-100 per night for a hotel room because your airline decided to strand you. Plan 5 years as FO and 5 years as CA as a starting scenario. How quickly you upgrade to CA and how successful you are in the career depends on how close your stars are to full alignment.

Here's something to get you started:

Expenses:
Cell Phone
Car - Insurance
Car - Payment
Car - Gasoline
Car - Maintenance
Crash Pad
Rent
Food
Utilities
Loan - College
Loan - Flight School (if you must, but you've been warned)
Credit Cards
Entertainment
Miscellaneous (toiletries, take a chick out, treat yourself to dinner)
Savings
Investments

Income:

Airline - Pay
Other Sources
2nd Job
3rd Job
4th Job
...
...

Spread this out over the course of 5 years and see what the financial picture looks like. Then do it for 10 years because it's possible you may be at the regional airline for that long. Don't forget to do this again at the major airline you want to end up at. And do the analysis there as well. And if you really want to make yourself sick, compare airline pay over 15 years to an average salaried job at $50,000/year with a 2% year over year increase. I did this once and figured out that if I go airline, I would have lost over $1.5 million in pay over the course of 10 years. Do you need a barf bag yet?

Your mileage may vary, and only you can truly know if the math makes sense. Wanting to fly is the easy part. But as you indicated, having a warm roof over your head is pretty neat too.