No one has mentioned the fact that he's taking out student loans to fund his education. It'll cost approx. $40k just to get the certifications and depending on which university, you're attending, could cost another $40k in tuition for everything else. Finding a job to pay that debt down and raise a family is nearly impossible. It's bad enough that you'll live off of ramen noodles for almost a decade after you've finished school, but you'll still have $50-$100k of debt once you do land a decent job.
I wouldn't buy into the garbage a lot of the schools are feeding. They are out there to sell themselves, even if it means your soul. "oh sure, no worries, just talk to Sallie Mae, they'll hook you up."...not!
I really wouldn't factor your girlfriend into the equation, either. No offense, but from experience, gfs come and gfs go. Especially, girlfriends going to medical school. It's a tough life and there is little to no time for relationships in medical school, not serious relationships anyway. So, between you and your dreams and hers, it will eventually send you both in opposite directions, that's life.
But...factor in the money! Debt sucks! I promise, pilots don't make enough to pay that kind of debt off. Most regional pilots earn $16-$25k annually, starting salary. Where exactly are you drawing money from to pay those loans off? Not your salary! That's for your noodles, gas, car, insurance, and the cardboard box on the side of Motel 6.
That's your pessimism for the day.
If after all that, you still want to be a pilot, go for it. Just don't ever say no one warned you first.