What's the best way to configure multiple email accounts?

First time poster, just switched over from Blackberry to he iPhone yesterday. I use Mail, iCal, Address Book, iTunes, iWeb, and iPhoto. I have 2 Macs (a Macbook for work and an iMac for home) and an iPhone 3G.
Here's what I want to do:
1) I have 4 email boxes - work (pop3), gmail, yahoo, and mac (are gmail and yahoo imap or pop3?). I need them to all be on the iPhone and synched to each mac. It seems logical that if all the accounts and structure are on MobileMe, then it is the driver of messaging, not one of the Macs. (Is anyone else getting like 1-2 minute response time on MobileMe?) Even with pop3, shouldn't email originated from the iPhone be shown on the Macs? Right now, I have no record on my computer that I ever sent that message other than a "message sent" email in my inbox after the iPhone delivers the email.
2) I have a lot of my mail organized in folders under "On My Mac". I understand from the discussion board that these folders will not synch to MobileMe or the other devices. Question is, where should I move them to make it happen, and what will that look like on the iPhone? Do they have to go in subfolders to each account's inbox? That's a lot of data given the large number of attachments I have and thousands of emails.
3) Aren't iPhoto and iTunes supposed to be included in the MobileMe functionality? I can't figure out how to make that happen. I got photos and music on the iPhone through a physical synch. That doesn't get them on each of my Macs. Will that even work given each computer has to be specifically authorized to play purchased music?
Sorry, I know this is a lot of stuff in a single post, and believe it or not, I am not a technology dummy. But I am a busy guy and simply need to get this working. Apple's documentation is very sketchy.

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Thank you in advance!

OK, seeing as no-one replied (presumably because a lot of this information is on the forums in bits elsewhere) here's how I've got on so far.
Applications - just went through them. About the only one I needed was my media server app. Just downloaded and re-installed, had a quick look back though my email to find the license key and it all went on fine. Installation never seemed quite right on my old machine so solved that problem too.
Movies - New iMovies just copied across the clips and projects into their respective folders. Seems to have worked but haven't checked it all that thoroughly. Some duplicate footage here but I can trim this out at some point when I get a chance to go through here.
Documents - Just copied these across.
Photos - used an app called iPhoto Library Manager. You can download for free but have to pay to use the part that consolidates your libraries. Possibly if I was willing to spend a bit more time I could have got away without using this but given I didn't know the state of my different libraries and just how many duplicates I had this was too much of a convenience to ignore. Also got my library into a state where I can now spend a few hours organising it a bit better with Faces / Events etc.
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Thanks for your reply Nick101. I see my example was oversimplified. When I say "multiple groups of contacts over multiple users" I'm really referring to N groups of contacts over N users.
So I need to add Fred, who can access and sync Bob's contacts, Sally's contacts, and Common contacts, as well as Fred's contacts. Can I do it with OS X server?
You mention you keep your and your partner's contacts administered locally. What keeps you from administering them through OS X server as well?
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If instead you managed to create a new library within the same profile. click the icon to start iTunes and immediately press and hold down the shift key, keep holding until asked to create or choose a library. Click Choose and navigte back to your original which should be at <User's Music>\iTunes.
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Here are three different methods >
How to use multiple iPods, iPads, or iPhones with one computer, http://support.apple.com/kb/HT1495
This article > iOS: How to transfer or sync content to your computer, http://support.apple.com/kb/HT1296
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What's the best way to configure multiple email accounts?

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