OK, so you get a job flying for free. Great. You are off gaining some command hours.
Few months down the line, you ask to be paid, operator decides he is going to take the next one in line, offering to work for free.
You've just lost your sweet gig but that's OK, you have some command hours! Time to hit job number two and progress further.
You keep sending out resumes but no one is taking you. You start speaking to a recently hired pilot. He wanted some twin time so offered to work for free. Guess you aren't getting your second job without working for free after all.
You dig in, just for a little while, you'll get a paid job soon right. Job two, you gotta work for free now.
That's OK, in six months, you'll have some quals for job three. Surely that has to be a paid job. At least you hope it is because you don't have any money left...
The biggest problem for working for free is someone else can always afford to do it longer than you can to get to their goal. You aren't the first, you won't be the last and it most definitely isn't just a few of you from your group.
A lot of operators won't take you just because you offer to work for free either. Command time, ratings, availability and time on type account for most of it, followed by recommendations from those in the game.