Personally, I wouldn't ship to someone off eBay without tracking and insurance or you're asking for trouble.
It depends on many factors (value of item etc), but let me say this...
im buyer on ebay now for almost 7 years, got almost 350 packages, where only circa 20 of them was shipped as insured.
i have only two or three lost items during those years, fortunately they was cheap (512kb ram card, two magazines).