I'm running asterisk within a vmware image on top of an intel based server. That server is the main server for the house. The base is just a file and print server with a terabyte raid array for storing everything.
On the bare metal I run the free vmware server for linux with two images running all the time. The first is the asterisk server and all it's related functions. The second is my intranet server image which hosts the plone content management system, jinzora web based jukebox and streaming (it display lyrics along with every other type of meta data you might want), mythweb (web interface for mythtv), my dvd library index, ftp site, and misc other items. Each item will get it own plugin in the client at some point. Right now I writing the music piece.
I'm moving the Asterisk installation to an embedded system running
http://www.astlinux.org/. That is a custom linux distro that is configured for the
http://www.soekris.com/ Soekris embedded computer platform. This should free the server up to run another image. I like to test everything I'm working on in vmware before I go through the trouble of building a system for someone else who can't run vmware. If they can then I just give them the image and walk away. Anyways running three images on a 3Ghz P4 is pushing it.
I wonder if there is a web client for Ical offered by apple. I don't know. There are other good calender apps out there that might work for what you want. Having a mac as a simple controller at each point is cost prohibitive. Having a central mac and then just web clients is the way to go even if you have to hack it all together. That's what I'm doing. I just plan to use google calender instead of Ical. The google API means I can integrate it into anything I want and everyone can update it where ever they are. One of my main design goals is not to tie a user to a platform, location, or OS. The finally product cannot use things that have to run on a certain platform unless they allow interaction through some kind of open standard from any other platform and can be installed inside a vmware image or on an embedded system so that the sofware just becomes an appliance (I.E. Indigo and OSX). With vmware coming to OSX that base is covered.
An example of something that isn't allowed is anything that requires Internet explorer as a web browser. Using something like this instantly ties you to windows with no way out. On the other hand a web page simply hosted on windows but can be accessed with IE or firefox is ok. Although it won't be me that does that.
I want to continue the same model I use when consulting. Build a plugin based interface where the user is free to mix and match without having to rewrite the entire thing and a plugin infrastructure using vmware or any other cross platform virtualization technology. No parrelles unless they release windows and linux versions.
For example a client needs a web server, messaging server, and VOIP server to start their small business. Right now I sell them a dell dual xeon server and three preconfigured vmware images, one for each task. The management interface is simply a copy of plone with the web interfaces for each system (apache, asterisk, etc) embedded. If the client decided he wants to change the messaging server all he has to do is launch the new vmware image and change the links in plone.
Like I said, I hope a community project evolves to not only to share plugins to the client but also to share infrastructure components. There are to many cool pieces of kit out there for any one person to master.
Rant over. If you can run vmware then look at trixbox. That's a open source linux distro that includes asterisk and all the bells and whistles preconfigured for you. Took me 5 mins to get it up and running with a single extension after the download. Of course then I spent months tweaking the hell out of it. But that's the way it goes.