Your response here makes me think you may not be understanding the insurance mechanic completely - to clarify, you cannot earn back the money for your lost ship. When you die, you've either got the 5% deductible in the bank and can pay it at that moment to get it back, or you choose to take the Sidewinder. Once you pick the Sidey that's it, hence the sage advice to never undock unless you have at least enough to cover the current rebuy cost of whatever you're flying.
Well, don't forget the 200,000 credit loan you can get towards it if you don't have enough in your account.