How are they using Exchange? Is it a pirated copy, or did he get setup with Windows Small Business Edition?

Rest of my comments inline:

Joe User wrote:

Access his email from anywhere and have the same contents as local
and remote - IMAP

IMAP, OWA, or you can configure Outlook to do RPC over HTTP, so you can fire up Outlook on a workstation and get your Exchange mail without having to VPN in. It's *not* designed for "kiosk" type use -- he'd want to use that on his home PC or something with a fast connection.

You also need to either setup a SSL cert - you can self sign (but you need to setup a CA) or buy a cert. Buying one is the best/easiest/most compatible way of doing it.

Ability to read and write email on phone currently uses Alltel as a
carrier. - ???

If it's a Windows Mobile or Palm phone -- no problem. Anything else you're looking at doing IMAP.

Wants to share Outlook calendars between his wkst's - Exchange.

Yup, or Google Apps.

His exchange has been running 6 months and the guy that did it for
him is a fly-by-niter and is not terribly dependable.

So 5 people - still hosted looks smarter. I just need to find him a
good host don't you think?

Hosted would be more secure and reliable, but if he's shelled out for Exchange, it's hard to justify it. Plus migrating off Exchange might be a pain.

Don't forget that he should get a good anti-spam/anti-virus package, or a hardware box like a Barracuda, or get a hosted MX solution like MessageOne, Postini, etc.

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