I think I understand the choice you're trying to make, and I'll give you my opinion as a current regional pilot who used to be a CFI.
Firstly, good idea on not whoring yourself and paying for a type rating.
Never understood that mentality.
In your honest opinion, upon moving back to the States, do you think the average pilot/CFI would struggle with either;
- - getting a fairly decent CFI job (assuming I am prepared to move around);
- - and then advancing to the regionals, after a couple of years
On getting a CFI job, well it depends a lot on where you want to work. As a CFI, I made more money than I did in my first year as a regional pilot. Significantly more money. My flight school kept pretty busy though, and many of us logged 100+ hrs each month. In the busier flight training areas, it will be much easier for you to make money if you go to a busy school than if you teach at a county airport in Idaho.
On advancing to the regionals, once you meet the minimum qualifications (which will be an ATP as of Aug 2013), timing is everything. Today, most regionals want 1000TT and 100ME. Some new hires have been CFI's for ~1yr before getting hired. Others have had to wait 4 years. However, when hiring waves begin, the higher time pilots will usually get picked up first.
Do NOT buy this "pilot shortage" BS unless you also believe in the Easter bunny and the tooth fairy.
- - Might you yourself feel the need to move abroad in order to further your career?
I'm looking to do that right now. There are good jobs in the US. The most lucrative jobs (FedEx, UPS, Delta) all but require that you've flown with somebody on the inside who's willing to give you a recommendation. The rest (AAL, UAL etc.) will give a payoff only after you've reached the 10-12 year mark
as a captain. Granted, with the stagnation of most seniority lists today, most FO's will go directly to the top of the CA payscale. However, as somebody who's just looking to start, that payoff will be a minimum of 15-20 years from now.
- - From your point of view, does it seem that things will improve (opportunities, ‘terms and conditions’)?
Very difficult to say. The big issue for the last decade or so is scope. The majors have been giving more and more flying away to regional carriers. More than half of all domestic flying is done by regionals. As regionals have grown, majors have become smaller, thus the number of higher paying Major jobs has fallen in favour of lower paying regional jobs. At one point, regionals used to be seen as stepping stones. Now, a growing number of pilots are seeing their regional airline as their career destination.
Right now, everybody is watching the Delta TA, with particular interest in the regional flying section.
If I were you, I'd try my level best to find a job outside of the US
Don't let sevenstrokeroll scare you either. Many CFI's and regional pilots are not US citizens. In my new hire class, 3 or 4 were permanent residents. It would be illegal for an employer not to hire you on that basis.
Airline Pilot Central is a great place to ask questions on US flying.
Feel free to PM me if you have any more questions.