Starter Equipment Purchase

That's a mighty nice collection of tools, the same kind of stuff I have for making projects that will be finished items.
For just plugging parts into a solderless breadboard, I would say it's a bit overkill.
My projects usually involve several ICs in addition to an arduino, that size breadboard is very undersized. 2 chips, some LEDs, all of sudden you're out of room.
I'd say $100 is a reasonable price to get all that at once.

For experimenting & working out designs, I have 3 65-row breadboards with power columns stuck on a clear plastic clipboard with a Duemilanove screwed down. Has been working out very well, nice & stable. The clip on top also helps secure wires that go off to actual devices.

If you are making anything with a decent # of connections, then getting some cards like these
http://www.vellemanusa.com/us/enu/product/view/?id=350322#
makes a great platform to assemble on.I do a lot of digital stuff with wirewrap. I don't see any wirewrap tool or 30 guage wire in that collection.
Get some socket strips as well
http://www.marcospecialties.com/product.asp?ic=SIP20L, gravitech.us also carries them, but you have to ask for them.
What do you have for schematic capture to document your designs? I see a lot of folks here use eagle. I use expresspcb.com, simple schematic capture, easy to create new parts if they're not in the library (I made myself a pro-mini foe example) , I use the PCB design part to show my layouts and play around with the fit of the parts on a board.
This thread shows the kind of things you can do easily with it, scroll down to the bottom:
http://www.arduino.cc/cgi-bin/yabb2/YaBB.pl?num=1289437587/4