Some comments on paying for training / time:
I was in Handsprings position a few years back, having spent 10 years working on aquiring my ratings and building my hours while working 75 hours a week to suport my family and pay for my flight lessons. After this hard work and sacrifice I found myself with a commercial multi engine certificate and an instructors certificate with instrument and multi engine ratings along with about 800 hours total and about 120 hrs multi.
I showed my face and resume (CV) to every charter operator in the LA area with no luck. I was able to get a job as a flight instructor and after 6 months I had aquired enough total and multi engine time to get a job flying C402's over the grand canyon which in turn led to an F/O job on a westwind. All of these jobs were low paying but after another year I made captain on the westwind and finally started to make decent money.
It was as a captain on the westwind that I flew with overseas F/O's who had paid for their time, most of whom had between 600 and 1500 hours. When I heard how they had paid their way in, I had to admit that if I had been aware of the opportunity a few years previous and had the money, (Which I didn't) I would have deffinitely taken it.
Being able to pay for a position only gets you in the door, you still have to prove yourself. I recall one fellow I flew with who had the flight talent of a penguin, needless to say, despite his money he didn't last long. As I mentioned in my original post, two other fellows had some talent and worked very hard and were able to turn their investments into successfull careers.
More recently I found that our aircraft was being sold and decided I wanted to make the step up to the larger Gulfstream. Getting into a Gulfstream I have discovered is much like getting into your first jet; you can only get a jet job if you have jet time, but you have to have a jet job to get jet time.
I decided that I would make my own opportunities and pay for my own Gulfstream type in order to get my foot in the door.
Fortunately I was offered a position in an older Gulfstream, so I won't have to pay my own money and I'm off to Gulfstream school in March at someone else's expense.
I have been fortunate and have not had to pay for my jet time or type ratings, I did have to pay for all my certifcates (Except my ATP) and some 120 hours or so of multi engine piston time.
Luck is what happens when preparation meets opportunity.
The question is what are you willing to do in order to be prepared.
You may not want to spend your own money for a future employer's benefit, but you can bet that others will, it may not be fair or right, but it's just the way it is.
I wish the best of luck to both those who are willing to spend as well as those that are not.