My urban EDC would be to replace the Supertool with my old PST, and have it be side-kicked by my Victorinox in my Pack-Rat. That would be about it. That Leatherman is basically a part of me, and I would hate to loose it through some stupid government feel good operation. And with luck, I could convince someone to let me smuggle my Supertool through like my glasses. So long as it isn't a cavity search, I WILL save my Supertool.
Putting the data recover and security tool kit onto a fresh thumb drive would be a pain in the butt, but that would most be trying to find a write-protectable usb drive that I liked the form factor of.
Other than that, there is nothing I carry that I would get all that worked up about if I lost it. I'd be out maybe week's pay, with the most expensive item being my calculator (and I don't really like the TI-83 I carry in my 'rat; there is a reason the -89 stays home). If I'm near anything terribly interesting and worth destroying, I might not even carry my medicine pouch, and that is heresay for me. I'd rather have my guides annoyed with me than lose that.
(For those of you who don't know the reference, imagine kicking your patron saint/gaurdian angel/ancesotry spirit/best friend in the shins and telling him/her/it you need to go it alone for a bit. You become a very unpopular mortal for a little while.)
I guess what I'm saying is, don't get too attached to your EDC. Too many ways to loose it.