I agree, we need a new lobby on here called "nanobrewtalk.com"! Take it from me - you're in for an adventure! Lots of ways to skin this cat, thus no one here has the definitive answer to all your questions. That being said, there are lots of great ideas in any of these nano brewery threads.
Check out my thread for 55 gallon false bottom ideas. Could be helpful to you. I get mine from Jaybird today and I'll update how it all fits.
http://www.homebrewtalk.com/f51/55-gal-drum-mash-tun-false-bottom-ideas-138941/
Regarding the chiller, get the biggest you can find. Its just a matter of time to cool, so it really depends on how long you're willing to allow your wort to cool. I found a big boy on ebay.
Also, I might suggest a side drain for your kettle, just above the bottom. No sense in whirlpooling if you drain out the bottom through a screen. Whirlpooling is effective for side draining kettles, because the perimeter of the vessel has the least amount of solids after the whirlpool.