Well, lets work out some times here:

Age 35- Pass CFI check ride, instruct for two years.

Age 37- hired at regional.

Age 44 - hired at major

Age 60 (going off UAL, DAL, AA average) - upgrade to captain in the smallest fleet type.

Age 65- retire.

It doesn't seem possible to me to jump from Capt in smallest type to the largest in 5 years.

PC12Luvr, if you are fully committed to chasing a career as a pilot then I say get your ratings and flight time AS SOON AS POSSIBLE! If this means taking out a loan do it, just make sure you make those payments on time.

Also, you will see and hear all about how regional pilots "live in poverty" but since you are already working two jobs and say it will take you 2 years to scrape up the cash to reach the CFI level I'm assuming you're already used to barely getting by. 3 years at the average regional and a guy will be making close to 40k. I can't speak from your perspective but compared to my $9.60 an hour job driving a delivery truck, 30-40k might as well be a million. And that quickly jumps up into the 50 and 60k range (if you don't get furloughed).

It seems to me like most of the pilots complaining about low regional wages started their 747 captain lifestyles while they were still sitting right seat in a Saab. If I had a stay at home wife, two kids, a mortgage, a BMW payment and a 60 inch flat screen I would be ****ed about regional pilot pay too!