I think you're in a classic situation of blackhat-to-white/greyhat and I'm not talking about SEO. The whitehat security/hacking community is basically people who were hackers or convicted hackers that used their expertise and reputation to get big companies on their payroll. There's companies out there that look for software vulnerabilities to sell solely to governments. You can imagine they're doing pretty well. Also, I think you're underpricing yourself if you went for $2000 with option 1. If you're good, $10K/monthly should be a starting point.
Also, if you don't know already have this, I'd look to augment my skill-set with some programming/software penetration testing experience to have a more balanced outlook and resume.