You are correct the 500TT is an insurance requirement. There are ways around it. I was hired on a 206 last year at 275 hours. The insurance company agreed to cover me after I had 25 hours in type flying jumpers. So I flew with another pilot onboard for 25 hours and was covered. A lot of drop zones are struggling to get pilots due to the fact cape air and a lot of 135 operations are taking guys at the 500 hours and paying better. So just send them your resume and show them you are willing to work hard and never compromise the safety of the drop zone and they might work with you. Also get some 182 time that helps as well. Good Luck!