Mike,
Getting your ratings should be no problem, all you need is money, time, and talent.
The more you have of any one of these the less of the other two you'll need.
A part 141 course will let you get that Commercial ticket in fewer hours logged, but might take more calender time due to the stage requirements. Check with your local CFI to get their opinion. Then go to a different school and get a second and third opinion.
If you can fly every day you can knock out your ratings in short order.
I finished my Commercial in 30 days, and my CFI in 45. Working part time, flying and studying full time.
I also had a couple students (2 of about 100) go from zero to Private in 30 days. Full time studying, flying 2 lessons a day. Very tough.
Once you get your CFI, build time instructing. Right now 1000TT/100Multi will get you an interview at any regional. In a few years that could go up again.
I had an interview at XJT scheduled for 9/19/01 at 1100/100.
I got hired some time later at 2000/250.
A classmate had 900/100.
50k is easy to get at a large regional. Just make Captain. That takes anywhere from 2 to 10 years.
At NetJets 50k is near starting pay, but you need signifigantly higher times,
2500/500, iirc.
Keep in mind there is a major change of lifestyle. You will be away from home 3/4 of the time. It is hard on you and your family. There's a joke about pilots needing 2 ex-wives to qualify for a Captain's upgrade. Its got a grain of truth to it because this industry is not kind to people's marriages.
Flying is fun.
Instructing is fun.
Packing for a four day trip and staying in a dirtbag hotel isn't. Your kids crying because you put on your uniform isn't. Your wife having a crisis, and you can't do anything about it because you're 2000 miles away, isn't. Working every weekend, every holiday, your anniversary, your wife's birthday, isn't.
You do have the best corner office view in the world.
The river visual into LGA on a clear day may be worth the whole price of admission.
Greasing it in, in a snowstorm, in rough terrain, and having the cabin applaud will make your day.
But then scheduling will call and Junior Man(mandatory overtime) you. And your day off goes away. And you get stuck with a MX delay for 4 hours - so you don't get paid. You make it back to the hub after the last flight has left for your home town, or the flight is full of revenue pax, and you get bumped off the jumpseat, so you have to buy your own hotel room...
It is just a very different life as an airline pilot.