The thing is, I paid 300,000$ for that 500 hour discount (and 4 year bachelors). My student loan repayments are $1,800 for the next 15 years. I need a job that actually pays money! (like a regional paying 10k/month).

This is good advice, but easier said than done. Do you have any suggestions on how to find a non-121 job for a CFI with around 1000 hours? Also, wouldn't it take longer to get to the legacy if I don't go through the regionals?