[wp-hackers] Got a question for you all

[Shelly at Foolish Visions]

My boss is looking to create a site that I'm not sure can be done 
without a LOT of custom code being written.  I don't even know what to 
search for in this case to see if it's possible with already-existing 
plugins or some simple functions or something.  Basically, if it can't 
be done simply (with existing plugins and/or some small edits) then he 
doesn't want to do it - he doesn't want to get too involved with 
custom-plugins and testing and all that.  So I told him I'd ask you all 
- if anyone would know, I believe you would!

So, what we're looking to do:

WordPress site.  Owner of the site will maintain a database of 
newspapers and funeral directors within the state (we'll keep it local 
for now, but I can see this expanding to the entire country).  This 
database will contain contact information (phone numbers, email and 
snail mail addresses, hours of operation, fees, policies, etc.)

It will be a fee-based membership area.  When someone logs in, they can 
search by town or zip code, and it'll bring up all the funeral directors 
*or* newspaper publications within an X-radius.  End user should be able 
to click on one (or more) checkboxes to select the publication (or 
funeral director) and send a mass email containing an obituary.  File 
upload are a must - the end user should be able to upload an image to 
run in the paper.

I know, kind of a morbid subject, but that's what they're looking to do. 
  Initially, I was confused, because I thought it would be one person 
managing the database, but as it turns out, they *alsO8 need an area 
where each FD and newspaper editor can log in and change their info as 
needed.  So I figured you could use the usermeta/userextra stuff to add 
to the profile and let them edit that way.  But I didn't know if there 
were any already-available plugins, or some code you all could point me 
to that could make the rest pretty easy to establish.

Has anyone done anything like this?  He already has a database of zip 
codes that is supposed to be easily integrated into the search form (I 
haven't seen it yet, so I'm taking his word), but I don't know how I 
would make this member-based, and how to allow for the multiple-sending, 
and all that stuff.  (Sorry, I'm running on 3 hours of sleep and one cup 
of coffee, so I'm kind of rambling)

I'd appreciate any input/point in the right direction/smack in the back 
of the head you all could provide.  I know I could do this on my own if 
I had time, but I don't - which is why he's looking for something quick.

Thanks!

~Shelly