What a great thread. Let me encourage all of you who are working toward getting the ratings and the time to join the world of professional aviation.
First, the journey itself is fun. Enjoy flying small aircraft, without tight schedules, going when and where you want to go with friends. Enjoy manual flight controls, the feel of the aircraft, the smell of Avgas and smooth dawn flights. Enjoy the comaraderie of the folks at the airport.
Keep moving forward. Get your Multi, Inst, Comm, out of the way was soon as you can. Consider getting partners for an Apache, or Twin Commanche and get a couple hundred hours of multi time. A lot of doors will open for you and the Multi, Inst, Comm is the most bang for the buck.
This business is incredibly cyclical. This is both good an bad. Use it to your advantage. Now is a great time to pick up ratings. Prices are better than they will be, airplanes and instructors are available. (Two years ago it was hard to schedule a checkride - every examiner was up to their eyes in applicants!)
Several trends in the industry will help pilots in your current position. You already know about the retirement picture, the aging baby boomer group - so I will not belabor that point. You should also consider that the major airlines are going through fleet replacement. The capabilities of 40 to 110 seat aircraft now allow these to be dispatched on routes formerly flown by 727, 737, MD-88 and Folker equipment. Smaller airplanes mean more frequent service, which the passengers love, and more pilots for the same revenue seat mile capacity.
You should also follow the battles within ALPA to some degree. The battle wages over if domestic air carriers will be allowed to operate these aircraft, who will fly them and how they will be flown.
The RJ is to an MD-88 what a 767 is to a 747. The 767 came along and allowed service to smaller international destinations, with greater frequency. It replaced many three pilot 747's. However, ALPA does not understand this simple fact of fleet renewal. They allowed codeshare operators (like ASA and Comair) to perform the flying they did not want, flying small jets. Now as the majority of narrowbody domestic aircraft are up for replacement with small jets, it is a huge problem.
Hopefully by the time we get to fly together, we will have one list and you can hire in on an RJ and retire from a 777. Good luck to you
~~~^~~~
Fins to the Left!
P.S. I was 33 when I made the jump after living Seattle's life for 15 years. The first year pay was miserable, but by sitting on reserve away from base it was increased by a $1,000 a month, tax free. Very soon I will upgrade and make more than I ever made in management - plus the eyes have gone from 20/60 to 20/10. Doc says less stress and more looking out the window is to credit. It is a job I truly love - and these are the "bad times." Good luck - get prepared now for the opportunities to come.
I'll keep that in mind when I start looking for a CFI position (like, a year from now 
