I'm an IT person like you. If I were you I'd take my $150k less tax, and buy an aircraft like an RV or something similar. You could get an award winning RV6 or 7 for that much or less. With an income like yours you'll easily be able to afford to run it. You can go anywhere in the country in almost any weather, in comfort, high speed (150'ish knots) and you'll still be earning more money than you ever will flying commercially. You'll also be able to take family and friends for a fly which you won't be able to do in an airline. When you're done, you can sell it and get your money back. You'll live the comfortable lifestyle you are accustom to, fly on your terms, with no politics and have a great time