My lack of health insurance is what has kept me from jumping for almost an entire year now. I hate being grounded, but to risk the possibility of ruining myself financially for what could be the rest of my life...well, that just isn't worth it to me. The sky will still be there when I finally get insurance again, and then I can jump all I want.
I always try to frame things in a "what would I regret later" kind of way. If I jump and get hurt and end up in unbelievable debt, I'll hate myself for being such a moron and jumping without insurance. If I wait until I get health insurance, I won't have anything to regret...I won't necessarily enjoy the time out, but I also won't be paying for it for the rest of my life.
Edited to add: another thing to consider is that if you do jump and get hurt, those medical bills may keep you from having the financial means to jump for a long time...which could effectively put a complete end to your skydiving career. Celebrate we will because life is short but sweet for certain