Ok, thoughts on this?
I just picked some random words... most of which are associated with geography.
I'd start a new thread with this since it's kind of a different animal than the rest of this thread.
This is an attempt at the second "Medium" level above.
Find something that is associated with the words below from the following regions
US Regions
WA/OR...................Rainfall
CA.........................Beach
HI/AK/Puerto Rico...Coast
NV/AZ/UT/NM..........Dry
ID/MT/ND/SD..........Population
WY/CO...................Peak
TX..........................Big
NE/KS/OK...............Twister
MN/WI....................Home
IA/MO/IL/AR...........Central
LA/MS/AL................Gulf
MI/IN/OH/PA...........Industry
WV/HK/TN...............Appellation
FL/GA.....................Heat
SC/NC/VA...............Atlantic
MD/DC/DE/NJ..........Colony
NY...........................City
CT/RI/MA.................Patriot
VT/NH/ME.................Maple
Extra Credit
Canada..............................Tank
Mexico / Central America.....Paradise
South America....................Frontier
Africa.................................Predator
Europe...............................Castle
Asia...................................Harmony
Australia.............................Crab
Hopefully this list of words isn't offensive to anyone. Part of the reason I'm thinking that keeping things less specific (like 'a cheesehead hat from WI') is to let people be more creative and get some more creativity going. Show me WI isn't all about cheese for example
For logistics, I haven't asked yet, but someone on AT nearby me that can collect the items from people and then physically deliver (rather than mail) the completed group of items to me might be preferred. HomeBrewerDude would be my first thought since I see him almost every weekday

If I want to be lame, I could make it my work address and then have stuff sent to me at work. That's a bit pointless though since the "goal" here is to get an address to send stuff to me directly.
Additional rules that have not been covered already by silverpig could be that the item doesn't necessarily have to be mailed from that region, but it does have to originate there.
For example, if I had Antarctica on the list and I had "barren" as the word, maybe you went to Antarctica and brought some rocks back to California where you live. Since they're originally from Antarctica, it's all good even though they're sent from CA.
Maybe mailing rocks isn't very cost effective though
Thoughts?
EDIT: HomeBrewerDude said I could PM people his work address so they could send objects there. He mentioned a weight / size limit though since it will be going through the mail department at work. (Don't send a bowling ball or a duffel bag full of packing peanuts)