What would you do in my case?

[1] wait for the package to miraculously appear 
(or months later) while realizing that it may 
never come...

or [2] file for insurance and just ask the Post 
Office (if I can believe their customer service 
to be that good) to notify me if the package is 
ever found?

or something else?

As for the deadbeat relative, I had to bail him 
out of jail at $6,900 originally.  He paid me 
back $4400... but I later learned that he just 
borrowed money from someone else.

Still, personally I feel that I shouldn't be 
entitled to any major purchasing for myself if I 
didn't take care of my friends and family first 
(especially when they're in need).  I wouldn't 
feel arlight, otherwise.