Not sure why offering to fly for free is a bad thing! It's not that I intend to do it forever. I am just trying to get some initial hours to at least have a chance at a paid job. It has nothing to do with de-valuing what I can offer. I'm not a "bad pilot" or "unsafe." I have some friends that work as successful freelance graphic designers that told me they had to offer their services for free to get some initial reviews (then started charging thereafter). I know a personal trainer that worked with a few clients (for free) to get a few testimonies to start charging for his services. Working for free (initially) is very common in other industries so I think it is bizarre that it is frowned upon in this industry.
To take on so much debt should already demonstrate some kind of commitment to the game. Being in debt with no job does not feel good at all, with someone in our group falling into a mild depression/regret for having chosen this career path.
So thanks for the harsh replies.